First Synthesis of a C‐Homosteroid from Pregn‐4‐ene‐3,11,20‐trione |
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| Authors: | Zonglei Zhang Lizhong Wang Xiaoqin Bian Qian Sun Hangxian Xu Cunde Wang |
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| Institution: | 1. School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, P.?R. China, (phone: +86‐514‐8797‐5568;2. fax: +86‐514‐8797‐5244);3. Department of Environmental and Chemical Engineering, Taizhou Polytechnic College, Taizhou 225300, P.?R. China |
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| Abstract: | (3α,5α)‐3‐Hydroxy‐C‐homopregnane‐11,20‐dione ( 3 ) was prepared in eleven steps from the commercially available pregn‐4‐ene‐3,11,20‐trione ( 4 ) via the 11‐oxo‐13‐formyl‐12,13‐secopregnane intermediate 11 (Scheme 2). Subjection of this secopregnane to an intramolecular aldol condensation afforded the α,β‐unsaturated key intermediate C‐homopregn‐12‐en‐11‐one 12 . |
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| Keywords: | C‐Homopregnane‐11 20‐dione 3α ‐hydroxy‐ 4‐Pregnene‐3 11 20‐trione Aldol condensation Chugaev reaction Ozonolysis |
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