An efficient synthesis of trans-gamma-oxo-alpha,beta-unsaturated carboxylic acids, the intermediates for patulolide A and pyrenophorin

Authors
Davis, KJ Bhalerao, UT Rao, BV
Citation
Kj. Davis et al., An efficient synthesis of trans-gamma-oxo-alpha,beta-unsaturated carboxylic acids, the intermediates for patulolide A and pyrenophorin, I J CHEM B, 40(8), 2001, pp. 656-661
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
40
Issue
8
Year of publication
2001
Pages
656 - 661
Database
ISI
SICI code
0376-4699(200108)40:8<656:AESOTC>2.0.ZU;2-H
Abstract
An efficient synthesis of intermediates for macrolide antifungals patulolid e A 14 and pyrenophorin 16 are described with the key steps involving (i) c oupling of the alkyl lithium with alpha,beta -unsaturated aldehyde 8, (ii) the oxidation of the cis-trans mixture of alpha -oxo-alpha,beta -unsaturate d aldehyde to the trans-gamma -oxo-alpha,beta -unsaturated carboxylic acid 12.