Synthesis of chiral intermediate (3S,5S,6S)-3,7-dimethyl-5,6-dihydroxy-7-en-octanal of didemnaketals analogue

Authors
Citation
Yx. Jia et al., Synthesis of chiral intermediate (3S,5S,6S)-3,7-dimethyl-5,6-dihydroxy-7-en-octanal of didemnaketals analogue, CHEM J CH U, 22(4), 2001, pp. 584-586
Citations number
6
Language
CHINESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE
ISSN journal
0251-0790 → ACNP
Volume
22
Issue
4
Year of publication
2001
Pages
584 - 586
Database
ISI
SICI code
0251-0790(200104)22:4<584:SOCI(>2.0.ZU;2-A
Abstract
A stereoselective synthesis of (3S,5S,6S)-3,7-dimethyl-5,6-dihydroxy-7-en-o ctanal, a key intermediate, for the synthesis of the HIV-inhibitory didemna ketals analogue, was performed via a series of reactions from the natural()-pulegone. In this approach, an interesting and valuable diastereo-recogni zable reaction between tertiary hydroxyepoxides and PCC was found. Therefor e, the mixture of compounds 8 and 9 was treated with PCC to recover 8 in 93 % yield and de 98% purity.