Efficient Synthesis of α-Benzylidene-γ-methyl-γ-butyrolactones

A concise synthesis of α‐benzylidene‐γ‐methyl‐γ‐butyrolactones 5a–g from substituted benzaldehydes is described. Compounds 1a–g on reaction with phosphorane 2, provide the pentenoates 3a–g, which can be hydrolyzed to the acids 4a–g. The latter are cyclized to the corresponding butyrolactones 5a–g in...

Full description

Saved in:
Bibliographic Details
Published inHelvetica chimica acta Vol. 85; no. 10; pp. 3525 - 3531
Main Authors Mali, Raghao S., Babu, Kantipudi N.
Format Journal Article
LanguageEnglish
Published Basel WILEY-VCH Verlag 01.10.2002
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
HALIDES
LIGNAN LACTONES
(+/-)-GADAIN
CARBONYLATION
CHEMISTRY
STEREOSELECTIVE SYNTHESIS
JATROPHA-GOSSYPIFOLIA LINN
Online AccessGet full text

Cover

More Information
Summary:A concise synthesis of α‐benzylidene‐γ‐methyl‐γ‐butyrolactones 5a–g from substituted benzaldehydes is described. Compounds 1a–g on reaction with phosphorane 2, provide the pentenoates 3a–g, which can be hydrolyzed to the acids 4a–g. The latter are cyclized to the corresponding butyrolactones 5a–g in excellent yields. The pentenoates 3a–g, on acid catalyzed cyclization, also provide 5a–g in very high yields.
Bibliography:ark:/67375/WNG-B1SFPWTK-4
ArticleID:HLCA3525
istex:FB2ADE709F266C1C4D4AC76A10C1FC8F62B930EE
Present Address: North Maharashtra University, Jalgaon–425 001, India (fax: +(91) 0257‐252183).
ISSN:0018-019X
1522-2675
DOI:10.1002/1522-2675(200210)85:10<3525::AID-HLCA3525>3.0.CO;2-#