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Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction
- 1.0345044 - ÚOCHB 2011 RIV US eng J - Journal Article
Šťastná, Eva - Černý, Ivan - Pouzar, Vladimír - Chodounská, Hana
Stereoselectivity of sodium borohydride reduction of saturated steroidal ketones utilizing conditions of Luche reduction.
Steroids. Roč. 75, č. 10 (2010), s. 721-725. ISSN 0039-128X. E-ISSN 1878-5867
R&D Projects: GA ČR(CZ) GA203/08/1498; GA MŠMT(CZ) LC06077
Institutional research plan: CEZ:AV0Z40550506
Keywords : steroid * synthesis * stereoselectivity
Subject RIV: CC - Organic Chemistry
Impact factor: 3.106, year: 2010
A series of keto steroids were reduced with sodium borohydride in the presence of cerium(III) chloride or samarium(III) iodide (Luche reduction). The ratios of axial and equatorial alcohols were determined by HPLC and the results were compared with those obtained by a standard sodium borohydride reduction. The best results were obtained with the 2-keto derivative 1, 7-keto derivatives 5 and 6, and 12-keto derivative 8.The Luche reduction of the 20-keto derivative 11 improved the proportion of the (20S)-alcohol in a mixture of (20S)/(20R) alcohols.
Permanent Link: http://hdl.handle.net/11104/0186411
Number of the records: 1