Citation
I. Izzo et al., Efficient stereocontrolled access to 15-and 16-hydroxy steroids, EUR J ORG C, (12), 1999, pp. 3505-3510
Citations number
52
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X
→ ACNP
Issue
12
Year of publication
1999
Pages
3505 - 3510
Database
ISI
SICI code
1434-193X(199912):12<3505:ESAT11>2.0.ZU;2-I
Abstract
Four epimeric 15- and 16-hydroxy steroids have been stereoselectively synth
esized from epi-androsterone. The key intermediate is the 3 beta-[(tert-but
yldimethylsilyl)oxy]-5 alpha-23,24-bisnorchol-16-en-22-ol (10), which allow
s both efficient D-ring functionalization and the possibility of facile sid
e-chain construction. In the course of this synthesis, we have found that t
he stereochemical outcome of the C-15 carbonyl reduction is strongly depend
ent on the C-16 and C-17 hybridization.