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

Liebigs Annalen der Chemie

Synthese von 4??Penten??4??oliden (γ??Methylen?螃摸?butyrolactonen) über 4??Pentensäuren

HJ Günther, E Guntrum, V Jäger

Index: Guenther, Hans Juergen; Guntrum, Eberhard; Jaeger, Volker Liebigs Annalen der Chemie, 1984 , # 1 p. 15 - 30

Full Text: HTML

Citation Number: 15

Abstract

Abstract 4-Penten-4-olide (γ-Methylen-γ-butyrolactone) 7 sind aus Allylalkoholen 1 durch Orthoester-Claisenumlagerung und Hydrolyse zu 4-Pentensäuren 5, anschließende Iodlactonisierung und HI-Abspaltung mit 1, 8-Diazabicyclo [5.4. 0] undec-7-en (DBU) in guter Gesamtausbeute und variablem Substitutionsmuster leicht zugänglich.—Die Iodlactonisierung unter kinetischer Kontrolle zeigt mäßige 1, 2-oder 1, 3-asymmetrische ...

1,1,1-triethoxy-3-methoxypropane Structure

1,1,1-triethoxy...

Allyl alcohol Structure

~%

2-(methoxymethyl)pent-4-enoic acid Structure

2-(methoxymethy...

3-ethenyl-3,7-dimethyloct-6-enoic acid Structure

3-ethenyl-3,7-d...

~%

4-methyl-5-methylidene-4-(4-methylpent-3-enyl)oxolan-2-one Structure

4-methyl-5-meth...

cis-3,7-Dimethyl-2,6-octadien-1-ol Structure

cis-3,7-Dimethy...

~%

4-methyl-5-methylidene-4-(4-methylpent-3-enyl)oxolan-2-one Structure

4-methyl-5-meth...

4,5-dihydro-5-(iodomethyl)furan-2(3H)-pne Structure

4,5-dihydro-5-(...

~77%

γ-Methylene-γ-butyrolactone Structure

γ-Methylene-γ-b...

UNII:29HK385L3G Structure

UNII:29HK385L3G

~%

3-methyl-5-methylideneoxolan-2-one Structure

3-methyl-5-meth...

(-)-3-methyl-4-pentenoic acid Structure

(-)-3-methyl-4-...

~%

4-methyl-5-methylideneoxolan-2-one Structure

4-methyl-5-meth...

Diethyl diallylmalonate Structure

Diethyl diallyl...

~77%

3,8-bis(iodomethyl)-2,7-dioxaspiro[4.4]nonane-1,6-dione Structure

3,8-bis(iodomet...

2-Allyl-5-iod-4-pentanolid-2-carbonsaeure-ethylester Structure

2-Allyl-5-iod-4...

3,8-bis(iodomethyl)-2,7-dioxaspiro[4.4]nonane-1,6-dione Structure

3,8-bis(iodomet...

~90%

3,8-dimethylidene-2,7-dioxaspiro[4.4]nonane-1,6-dione Structure

3,8-dimethylide...

Diethyl diallylmalonate Structure

Diethyl diallyl...

~%

3,8-dimethylidene-2,7-dioxaspiro[4.4]nonane-1,6-dione Structure

3,8-dimethylide...

2-methylpropan-2-amine S-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl) O-methyl phosphorothioate Structure

2-methylpropan-...

~%

3,4,4-trimethyl-5-methylideneoxolan-2-one Structure

3,4,4-trimethyl...

2-(methoxymethyl)pent-4-enoic acid Structure

2-(methoxymethy...

~%

3-(methoxymethyl)-5-methylideneoxolan-2-one Structure

3-(methoxymethy...

3,8-bis(iodomethyl)-2,7-dioxaspiro[4.4]nonane-1,6-dione Structure

3,8-bis(iodomet...

~93%

2,7-Dioxaspiro[4.4]nonane-1,6-dione,3,8-dimethyl- Structure

2,7-Dioxaspiro[...

3(R,S)-phenyl-pent-4-enoic acid Structure

3(R,S)-phenyl-p...

~%

2-methyl-3-phenyl-2H-furan-5-one Structure

2-methyl-3-phen...

3-Phenyl-4-penten-4-olid Structure

3-Phenyl-4-pent...

3-Phenyl-2-propen-1-ol Structure

3-Phenyl-2-prop...

~%

2-methyl-3-phenyl-2H-furan-5-one Structure

2-methyl-3-phen...

5-(iodomethyl)-3,3-dimethyloxolan-2-one Structure

5-(iodomethyl)-...

~67%

3,3-dimethyl-5-methylideneoxolan-2-one Structure

3,3-dimethyl-5-...

3-Methyl-2-buten-1-ol Structure

3-Methyl-2-bute...

1,1,1-Triethoxypropane Structure

1,1,1-Triethoxy...

~56%

ethyl 2,3,3-trimethylpent-4-enoate Structure

ethyl 2,3,3-tri...

cis-3,7-Dimethyl-2,6-octadien-1-ol Structure

cis-3,7-Dimethy...

Triethyl orthoacetate Structure

Triethyl orthoa...

~%

3-ethenyl-3,7-dimethyloct-6-enoic acid Structure

3-ethenyl-3,7-d...

ethyl 2,3,3-trimethylpent-4-enoate Structure

ethyl 2,3,3-tri...

~75%

2,3,3-trimethylpent-4-enoic acid Structure

2,3,3-trimethyl...

tert-Butanol Structure

Triethyl orthoacetate Structure

Triethyl orthoa...

3-Methyl-2-buten-1-ol Structure

3-Methyl-2-bute...

~%

3,3-DIMETHYL-4-PENTENOIC ACID Structure

3,3-DIMETHYL-4-...

5-iodo-4-hydroxy-3,3-dimethylpentanoic acid lactone Structure

5-iodo-4-hydrox...

~80%

4,4-DIMETHYL-5-METHYLENE-GAMMA-BUTYROLACTONE Structure

4,4-DIMETHYL-5-...