Journal
STEROIDS
Volume 74, Issue 13-14, Pages 1073-1079Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.steroids.2009.09.001
Keywords
Glycospirostanes; Ring-closing metathesis; Polyhydroxylated compounds
Funding
- Polish Ministry of Science and Higher Education [PBZ-KBN-126/T09/2004, N N204 240334]
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Syntheses of glycospirostanes from 3 beta-hydroxy-23,24-dinor-5 alpha-cholano-22,16-lactone and 3 alpha-hydroxy-23,24-dinor-5 beta- -cholano-22,16-lactone were performed. The key step of these syntheses was ring-closing metathesis of the corresponding C,O-diallyl derivative. Further elaboration of the six-membered ring F consisted of allylic hydroxylation with SeO(2) followed by OsO(4) dihydroxylation of the C24-C25 double bond. The obtained final products proved to be simultaneously O- and C-L-arabinopyranosides. (C) 2009 Elsevier Inc. All rights reserved.
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