Efficient Stereocontrolled Access to 15- and 16-Hydroxy Steroids
作者： Irene Izzo , Marcello Di Filippo , Raffaella Napolitano , Francesco De Riccardis
DOI: 10.1002/(SICI)1099-0690(199912)1999:12<3505::AID-EJOC3505>3.0.CO;2-C
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摘要: 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 possibility of facile side-chain construction. In course this synthesis, we found that stereochemical outcome C-15 carbonyl reduction strongly dependent on C-16 C-17 hybridization.
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