Total synthesis of d,l-coronafacic acid by an intermolecular Diels-Alder approach

An efficient total synthesis of d,l-coronafacic acid ( 2 ) has been achieved from 4-cyclopentene-1,3-dione ( 4 ). The synthesis involves keto ester 7 as a key intermediate that is conveniently prepared by the Diels-Alder addition of enedione 4 to ethyl 4-ethyl-2,4-pentadienoate ( 5 ).

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Bibliographic Details
Published in:Canadian journal of chemistry 1984-01, Vol.62 (9), p.1747-1750
Main Authors: Liu, Hsing-Jang, Llinas-Brunet, Montse
Format: Article
Language:eng ; fre
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Description
Summary:An efficient total synthesis of d,l-coronafacic acid ( 2 ) has been achieved from 4-cyclopentene-1,3-dione ( 4 ). The synthesis involves keto ester 7 as a key intermediate that is conveniently prepared by the Diels-Alder addition of enedione 4 to ethyl 4-ethyl-2,4-pentadienoate ( 5 ).
ISSN:0008-4042
1480-3291
DOI:10.1139/v84-300