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Efficient Stereocontrolled Access to 15‐ and 16‐Hydroxy Steroids
Author(s) -
Izzo Irene,
Di Filippo Marcello,
Napolitano Raffaella,
De Riccardis Francesco
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199912)1999:12<3505::aid-ejoc3505>3.0.co;2-c
Subject(s) - chemistry , stereochemistry , androsterone , side chain , stereoselectivity , ring (chemistry) , surface modification , steroid , combinatorial chemistry , organic chemistry , catalysis , biochemistry , hormone , polymer
Four epimeric 15‐ and 16‐hydroxy steroids have been stereoselectively synthesized from epi ‐androsterone. The key intermediate is the 3β‐[( tert ‐butyldimethylsilyl)oxy]‐5α‐23,24‐bisnorchol‐16‐en‐22‐ol ( 10 ), which allows both efficient D‐ring functionalization and the possibility of facile side‐chain construction. In the course of this synthesis, we have found that the stereochemical outcome of the C‐15 carbonyl reduction is strongly dependent on the C‐16 and C‐17 hybridization.