e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Tetrahedron

Cembranolide total synthesis. Anisomelic acid

JA Marshall, BS DeHoff

Index: Marshall, James A.; DeHoff, Bradley S. Tetrahedron, 1987 , vol. 43, # 21 p. 4849 - 4860

Full Text: HTML

Citation Number: 44

Abstract

The stereoselective total synthesis of (±)-anisomelic acid (34) has been achieved starting from aldehyde 7, the ozonolysis product of geranyl acetate. Two key steps ensured the stereoselectivity of the synthesis. The first entailed a highly anti-selective addition of the ...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-7-(dimethoxyphosphinyl)-7-carbomethoxy-3-octenyl]-5-[(E)-4-formyl-2-methyl-1-butenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-7-(dimethoxyphosphinyl)-7-carbomethoxy-3-octenyl]-5-[(E)-4-formyl-2-methyl-1-butenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-7-(dimethoxyphosphinyl)-7-carbomethoxy-3-octenyl]-5-[(E)-4-formyl-2-methyl-1-butenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-7-(dimethoxyphosphinyl)-7-carbomethoxy-3-octenyl]-5-[(E)-4-formyl-2-methyl-1-butenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-7-(dimethoxyphosphinyl)-7-carbomethoxy-3-octenyl]-5-[(E)-4-formyl-2-methyl-1-butenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-7-(dimethoxyphosphinyl)-7-carbomethoxy-3-octenyl]-5-[(E)-4-formyl-2-methyl-1-butenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-7-(dimethoxyphosphinyl)-7-carbomethoxy-3-octenyl]-5-[(E)-4-formyl-2-methyl-1-butenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

(E)-methyl 2-(dimethoxyphosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

(E)-methyl 2-(d...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

(E)-methyl 2-(dimethoxyphosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

(E)-methyl 2-(d...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

(E)-methyl 2-(dimethoxyphosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

(E)-methyl 2-(d...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

(E)-methyl 2-(dimethoxyphosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

(E)-methyl 2-(d...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

(E)-methyl 2-(dimethoxyphosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

(E)-methyl 2-(d...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

(E)-methyl 2-(dimethoxyphosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

(E)-methyl 2-(d...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

(E)-methyl 2-(dimethoxyphosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

(E)-methyl 2-(d...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

(E)-methyl 8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-2-(dimethoxyphosphoryl)-6-methyloct-5-enoate Structure

(E)-methyl 8-((...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

(E)-methyl 8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-2-(dimethoxyphosphoryl)-6-methyloct-5-enoate Structure

(E)-methyl 8-((...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

(E)-methyl 8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-2-(dimethoxyphosphoryl)-6-methyloct-5-enoate Structure

(E)-methyl 8-((...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

(E)-methyl 8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-2-(dimethoxyphosphoryl)-6-methyloct-5-enoate Structure

(E)-methyl 8-((...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

(E)-methyl 8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-2-(dimethoxyphosphoryl)-6-methyloct-5-enoate Structure

(E)-methyl 8-((...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

(E)-methyl 8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-2-(dimethoxyphosphoryl)-6-methyloct-5-enoate Structure

(E)-methyl 8-((...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

(E)-methyl 8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-2-(dimethoxyphosphoryl)-6-methyloct-5-enoate Structure

(E)-methyl 8-((...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

(E)-6-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-4-methylhex-3-en-1-ol Structure

(E)-6-((2R,3R)-...

~93%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-6-iodo-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-6-iodo-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-6-iodo-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-6-iodo-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-6-iodo-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-6-iodo-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-6-iodo-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

rel-(ξ,4S,5S)-4-[(E)-3-methyl-6-iodo-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

(E)-6-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-4-methylhex-3-en-1-ol Structure

(E)-6-((2R,3R)-...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

(E)-6-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-4-methylhex-3-en-1-ol Structure

(E)-6-((2R,3R)-...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

(E)-6-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-4-methylhex-3-en-1-ol Structure

(E)-6-((2R,3R)-...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

(E)-6-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-4-methylhex-3-en-1-ol Structure

(E)-6-((2R,3R)-...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

(E)-6-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-4-methylhex-3-en-1-ol Structure

(E)-6-((2R,3R)-...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

(E)-6-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-4-methylhex-3-en-1-ol Structure

(E)-6-((2R,3R)-...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

(E)-6-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-4-methylhex-3-en-1-ol Structure

(E)-6-((2R,3R)-...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

rel-(2ξ,4S,5S)-4-[(E)-3-methyl-6-hydroxy-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(2ξ,4S,5S)-...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

rel-(2ξ,4S,5S)-4-[(E)-3-methyl-6-hydroxy-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(2ξ,4S,5S)-...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

rel-(2ξ,4S,5S)-4-[(E)-3-methyl-6-hydroxy-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(2ξ,4S,5S)-...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

rel-(2ξ,4S,5S)-4-[(E)-3-methyl-6-hydroxy-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(2ξ,4S,5S)-...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

rel-(2ξ,4S,5S)-4-[(E)-3-methyl-6-hydroxy-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(2ξ,4S,5S)-...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

rel-(2ξ,4S,5S)-4-[(E)-3-methyl-6-hydroxy-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(2ξ,4S,5S)-...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~99%

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

rel-(2ξ,4S,5S)-4-[(E)-3-methyl-6-hydroxy-3-hexenyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(2ξ,4S,5S)-...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

rel-(2ξ,4R,5R)-4-[(E)-3-methyl-3,5-hexadienyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-1-oxacyclopentan-2-ol Structure

rel-(2ξ,4R,5R)-...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

rel-(2ξ,4R,5R)-4-[(E)-3-methyl-3,5-hexadienyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-1-oxacyclopentan-2-ol Structure

rel-(2ξ,4R,5R)-...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

rel-(2ξ,4R,5R)-4-[(E)-3-methyl-3,5-hexadienyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-1-oxacyclopentan-2-ol Structure

rel-(2ξ,4R,5R)-...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

rel-(2ξ,4R,5R)-4-[(E)-3-methyl-3,5-hexadienyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-1-oxacyclopentan-2-ol Structure

rel-(2ξ,4R,5R)-...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

rel-(2ξ,4R,5R)-4-[(E)-3-methyl-3,5-hexadienyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-1-oxacyclopentan-2-ol Structure

rel-(2ξ,4R,5R)-...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

rel-(2ξ,4R,5R)-4-[(E)-3-methyl-3,5-hexadienyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-1-oxacyclopentan-2-ol Structure

rel-(2ξ,4R,5R)-...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

rel-(2ξ,4R,5R)-4-[(E)-3-methyl-3,5-hexadienyl]-5-[(E)-2-methyl-5-tert-butyldimethylsilyloxy-1-pentenyl]-1-oxacyclopentan-2-ol Structure

rel-(2ξ,4R,5R)-...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

(3aR,6E,10Z,14E,15aR)-methyl 2-hydroxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3aR,6E,10Z,14E...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

(3aR,6E,10Z,14E,15aR)-methyl 2-hydroxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3aR,6E,10Z,14E...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

(3aR,6E,10Z,14E,15aR)-methyl 2-hydroxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3aR,6E,10Z,14E...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

(3aR,6E,10Z,14E,15aR)-methyl 2-hydroxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3aR,6E,10Z,14E...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~87%

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

(3aR,6E,10Z,14E,15aR)-methyl 2-hydroxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3aR,6E,10Z,14E...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

(3aR,6E,10Z,14E,15aR)-methyl 2-hydroxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3aR,6E,10Z,14E...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

(3aR,6E,10Z,14E,15aR)-methyl 2-hydroxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3aR,6E,10Z,14E...

(E)-methyl 2-(dimethoxyphosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

(E)-methyl 2-(d...

~%

(3aR,6E,10Z,14E,15aR)-methyl 2-hydroxy-6,14-dimethyl-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3aR,6E,10Z,14E...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

methyl (E)-2-(bis(2,2,2-trifluoroethoxy)phosphoryl)-8-((2R,3R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

methyl (E)-2-(b...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

(3S,3aR,6E,10Z,14E,15aR)-methyl 3-(hydroxymethyl)-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3S,3aR,6E,10Z,...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

(3S,3aR,6E,10Z,14E,15aR)-methyl 3-(hydroxymethyl)-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3S,3aR,6E,10Z,...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

(3S,3aR,6E,10Z,14E,15aR)-methyl 3-(hydroxymethyl)-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3S,3aR,6E,10Z,...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

(3S,3aR,6E,10Z,14E,15aR)-methyl 3-(hydroxymethyl)-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3S,3aR,6E,10Z,...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

(3S,3aR,6E,10Z,14E,15aR)-methyl 3-(hydroxymethyl)-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3S,3aR,6E,10Z,...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

(3S,3aR,6E,10Z,14E,15aR)-methyl 3-(hydroxymethyl)-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3S,3aR,6E,10Z,...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

(3S,3aR,6E,10Z,14E,15aR)-methyl 3-(hydroxymethyl)-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3S,3aR,6E,10Z,...

(E)-methyl 2-(dimethoxyphosphoryl)-8-((2R,3R)-2-((E)-5-hydroxy-2-methylpent-1-en-1-yl)-5-methoxytetrahydrofuran-3-yl)-6-methyloct-5-enoate Structure

(E)-methyl 2-(d...

~%

(3S,3aR,6E,10Z,14E,15aR)-methyl 3-(hydroxymethyl)-6,14-dimethyl-2-oxo-2,3,3a,4,5,8,9,12,13,15a-decahydrocyclotetradeca[b]furan-10-carboxylate Structure

(3S,3aR,6E,10Z,...

(2E,6E)-6-methylnona-2,6,8-trien-1-ol Structure

(2E,6E)-6-methy...

~%

rel-(1R,14R)-(2E,6Z,10E)-3,11-dimethyl-7-carbomethoxy-17-oxa-16-oxabicyclo[12.3.0]hexadeca-2,6,10-triene Structure

rel-(1R,14R)-(2...

(E)-acetic acid 6-hydroxy-3-methylhex-2-enyl ester Structure

(E)-acetic acid...

~%

rel-(1R,14R)-(2E,6Z,10E)-3,11-dimethyl-7-carbomethoxy-17-oxa-16-oxabicyclo[12.3.0]hexadeca-2,6,10-triene Structure

rel-(1R,14R)-(2...

methyl (E,E)-6-methyl-2,6,8-nonatrienonate Structure

methyl (E,E)-6-...

~%

rel-(1R,14R)-(2E,6Z,10E)-3,11-dimethyl-7-carbomethoxy-17-oxa-16-oxabicyclo[12.3.0]hexadeca-2,6,10-triene Structure

rel-(1R,14R)-(2...

methyl (E,E)-6-methyl-7-formyl-2,6-octadienoate Structure

methyl (E,E)-6-...

~%

rel-(1R,14R)-(2E,6Z,10E)-3,11-dimethyl-7-carbomethoxy-17-oxa-16-oxabicyclo[12.3.0]hexadeca-2,6,10-triene Structure

rel-(1R,14R)-(2...

(2E,6E)-methyl 8-hydroxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl ...

~%

rel-(1R,14R)-(2E,6Z,10E)-3,11-dimethyl-7-carbomethoxy-17-oxa-16-oxabicyclo[12.3.0]hexadeca-2,6,10-triene Structure

rel-(1R,14R)-(2...

(2E,6E)-methyl-8-acetoxy-6-methylocta-2,6-dienoate Structure

(2E,6E)-methyl-...

~%

rel-(1R,14R)-(2E,6Z,10E)-3,11-dimethyl-7-carbomethoxy-17-oxa-16-oxabicyclo[12.3.0]hexadeca-2,6,10-triene Structure

rel-(1R,14R)-(2...

N,N-diisopropyl (E,E)-6-methyl-2,6,8-nonatrienyl carbamate Structure

N,N-diisopropyl...

~%

rel-(1R,14R)-(2E,6Z,10E)-3,11-dimethyl-7-carbomethoxy-17-oxa-16-oxabicyclo[12.3.0]hexadeca-2,6,10-triene Structure

rel-(1R,14R)-(2...

rel-(ξ,4S,5S)-4-[(E)-3-methyl-7-(dimethoxyphosphinyl)-7-carbomethoxy-3-octenyl]-5-[(E)-4-formyl-2-methyl-1-butenyl]-2-methoxy-1-oxacyclopentane Structure

rel-(ξ,4S,5S)-4...

~%

rel-(1R,14R)-(2E,6Z,10E)-3,11-dimethyl-7-carbomethoxy-17-oxa-16-oxabicyclo[12.3.0]hexadeca-2,6,10-triene Structure

rel-(1R,14R)-(2...

Stereoselective total synthesis of the cembranolide diterpen...

[Marshall, James A.; DeHoff, Bradley S. Tetrahedron Letters, 1986 , vol. 27, # 40 p. 4873 - 4876]