First total synthesis of xestobergsterol A and active structural analoguesof the xestobergsterols

Authors
Jung, ME Johnson, TW
Citation
Me. Jung et Tw. Johnson, First total synthesis of xestobergsterol A and active structural analoguesof the xestobergsterols, ORG LETT, 1(10), 1999, pp. 1671-1674
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
10
Year of publication
1999
Pages
1671 - 1674
Database
ISI
SICI code
1523-7060(19991118)1:10<1671:FTSOXA>2.0.ZU;2-7
Abstract
[GRAPHICS] A novel pentacyclic polyhydroxylated sterol, xestobergsterol A (la), has be en synthesized in 24 steps and in good overall yield from stigmasterol 17. The key steps of the synthesis are the Breslow remote functionalization of the polyoxygenated steroid derived from 25 and the base-catalyzed epimeriza tion-aldol condensation of the dione derived from 27.