前往化源商城

举例 :可输入Filippa Pettersson 或者 Cancer Res. 75(6) , 1102-12, (2015) 或者10.1002/anie.201600521

Tetrahedron Letters

Enantiospecific total synthesis of pseudomonic acids from arabinose

GWJ Fleet, MJ Gough, TKM Shing

文献索引：Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Letters, 1983 , vol. 24, # 34 p. 3661 - 3664

全文：HTML全文

被引用次数: 22

摘要

Pseudomonic acids A (I) and C (2) are members of a novel class of compounds with antibacterial and antimycoplasmal activity.' The first reported synthesis of racemic pseudomonic acid C involved a key step of coupling the racemic form of the pyranose aldehyde (3) with the ylid derived from the racemic form of the phosphonium salt (4)(Scheme 1). 2 Subsequent approaches to racemic3 pseudomonic acids have been directed ...

核糖结构式

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

1,5-Anhydro-D-arabinitol结构式

1,5-Anhydro-D-a...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

(3S,4s)-3-(2-羟基乙基)-3,4-二氢-2H-吡喃-4-醇结构式

(3S,4s)-3-(2-羟基...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL结构式

3-[2-(TERT-BUTY...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

2-((2S,5R)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)-N,N-dimethylacetamide结构式

2-((2S,5R)-5-(2...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

ethyl (E)-4-((3a'S,4'S,7'S,7a'R)-7'-(2-((tert-butyldiphenylsilyl)oxy)ethyl)tetrahydro-4'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4,5-c]pyran]-4'-yl)-3-methylbut-2-enoate结构式

ethyl (E)-4-((3...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

(S)-3,6-二氢-2H-吡喃-3-醇结构式

(S)-3,6-二氢-2H-吡喃-3-醇

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

5S-IODO-1S,6S-3,7-DIOXABICYCLO[4,3,0]-NONAN-8-ONE结构式

5S-IODO-1S,6S-3...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

2-(r)-3,6-二氢-2H-吡喃-3-基-N,N-二甲基乙酰胺结构式

2-(r)-3,6-二氢-2H...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

(E)-5,9-anhydro-6,7-O-cyclohexylidene-2,3,4,8-tetradeoxy-8-C-(ethoxycarbonyl)methyl-3-methyl-D-allo-non-2-enitol结构式

(E)-5,9-anhydro...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

1-((2S,5R)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-5,6-dihydro-2H-pyran-2-yl)propan-2-one结构式

1-((2S,5R)-5-(2...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

1-((2S,3R,4R,5S)-5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-3,4-dihydroxytetrahydro-2H-pyran-2-yl)propan-2-one结构式

1-((2S,3R,4R,5S...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

1-((3a'S,4'S,7'S,7a'R)-7'-(2-((tert-butyldiphenylsilyl)oxy)ethyl)tetrahydro-4'H-spiro[cyclohexane-1,2'-[1,3]dioxolo[4,5-c]pyran]-4'-yl)propan-2-one结构式

1-((3a'S,4'S,7'...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

INTEMEDIATE FOR MUPIRICIN结构式

INTEMEDIATE FOR...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

(E)-5,9-anhydro-6,7-O-cyclohexylidene-2,3,4,8-tetradeoxy-8-C-(ethoxycarbonyl)methyl-3-methyl-D-allo-non-2-enal结构式

(E)-5,9-anhydro...

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

Ethyl monate C结构式

~%

Pseudomonic Acid C结构式

Pseudomonic Acid C

N,N-二甲基乙酰胺二甲基缩醛结构式

N,N-二甲基乙酰胺二甲基缩醛

(S)-3,6-二氢-2H-吡喃-3-醇结构式

(S)-3,6-二氢-2H-吡喃-3-醇

~82%

2-(r)-3,6-二氢-2H-吡喃-3-基-N,N-二甲基乙酰胺结构式

2-(r)-3,6-二氢-2H...

核糖结构式

~%

2-(r)-3,6-二氢-2H-吡喃-3-基-N,N-二甲基乙酰胺结构式

2-(r)-3,6-二氢-2H...

(3S,4s)-3-(2-羟基乙基)-3,4-二氢-2H-吡喃-4-醇结构式

(3S,4s)-3-(2-羟基...

叔丁基二苯基氯硅烷结构式

叔丁基二苯基氯硅烷

~90%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL结构式

3-[2-(TERT-BUTY...

核糖结构式

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL结构式

3-[2-(TERT-BUTY...

1,5-Anhydro-D-arabinitol结构式

1,5-Anhydro-D-a...

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL结构式

3-[2-(TERT-BUTY...

(S)-3,6-二氢-2H-吡喃-3-醇结构式

(S)-3,6-二氢-2H-吡喃-3-醇

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL结构式

3-[2-(TERT-BUTY...

5S-IODO-1S,6S-3,7-DIOXABICYCLO[4,3,0]-NONAN-8-ONE结构式

5S-IODO-1S,6S-3...

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL结构式

3-[2-(TERT-BUTY...

2-(r)-3,6-二氢-2H-吡喃-3-基-N,N-二甲基乙酰胺结构式

2-(r)-3,6-二氢-2H...

~%

3-[2-(TERT-BUTYL-DIPHENYL-SILANYLOXY)-ETHYL]-3,4-DIHYDRO-2H-PYRAN-4-OL结构式

3-[2-(TERT-BUTY...

1,5-Anhydro-D-arabinitol结构式

1,5-Anhydro-D-a...

~%

(S)-3,6-二氢-2H-吡喃-3-醇结构式

(S)-3,6-二氢-2H-吡喃-3-醇

核糖结构式

~%

(S)-3,6-二氢-2H-吡喃-3-醇结构式

(S)-3,6-二氢-2H-吡喃-3-醇

5S-IODO-1S,6S-3,7-DIOXABICYCLO[4,3,0]-NONAN-8-ONE结构式

5S-IODO-1S,6S-3...

~87%

(3S,4s)-3-(2-羟基乙基)-3,4-二氢-2H-吡喃-4-醇结构式

(3S,4s)-3-(2-羟基...

核糖结构式

~%

(3S,4s)-3-(2-羟基乙基)-3,4-二氢-2H-吡喃-4-醇结构式

(3S,4s)-3-(2-羟基...

(S)-3,6-二氢-2H-吡喃-3-醇结构式

(S)-3,6-二氢-2H-吡喃-3-醇

~%

(3S,4s)-3-(2-羟基乙基)-3,4-二氢-2H-吡喃-4-醇结构式

(3S,4s)-3-(2-羟基...

2-(r)-3,6-二氢-2H-吡喃-3-基-N,N-二甲基乙酰胺结构式

2-(r)-3,6-二氢-2H...

~%

(3S,4s)-3-(2-羟基乙基)-3,4-二氢-2H-吡喃-4-醇结构式

(3S,4s)-3-(2-羟基...

1,5-Anhydro-D-arabinitol结构式

1,5-Anhydro-D-a...

~%

(3S,4s)-3-(2-羟基乙基)-3,4-二氢-2H-吡喃-4-醇结构式

(3S,4s)-3-(2-羟基...

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]

Total synthesis of pseudomonic acid C

[Barrish, Joel C.; Lee, Hsi Lin; Mitt, Toomas; Pizzolato, Giacomo; Baggiolini, Enrico G; Uskokovic, Milan R Journal of Organic Chemistry, 1988 , vol. 53, # 18 p. 4282 - 4295]