A CONVENIENT STEREOSELECTIVE SYNTHESIS OF CASTASTERONE AND ITS ANALOGS USING ARSENIC YLIDES

Authors
WERNER F PARMENTIER G LUU B DINAN L
Citation
F. Werner et al., A CONVENIENT STEREOSELECTIVE SYNTHESIS OF CASTASTERONE AND ITS ANALOGS USING ARSENIC YLIDES, Tetrahedron, 52(15), 1996, pp. 5525-5532
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
15
Year of publication
1996
Pages
5525 - 5532
Database
ISI
SICI code
0040-4020(1996)52:15<5525:ACSSOC>2.0.ZU;2-0
Abstract
(2 alpha,3 alpha,22S)-Trihydroxy-5 alpha-cholestan-6-one 3 and (2 alph a,3 alpha,22R)-trihydroxy-5 alpha-cholestan-6-one 4 have been synthesi zed with high stereoselectivity. The key step is the coupling of the a ldehyde 5 with an arsenic ylide, followed by an in situ DIBAH reductio n. A second arsenic ylide was used to prepare the key allylic alcohol intermediate 15, which allows the synthesis of castasterone 2. Copyrig ht (C) 1996 Elsevier Science Ltd