A new approach toward the synthesis of C,D-cis coupled steroid and C,D-cis coupled d-homosteroid skeletons |
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| Authors: | Svetlana Dratch Tanya Charnikhova Florence CE SarabèrBen JM Jansen Aede de Groot |
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| Institution: | a Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands
b Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Kuprevich str. 5/2, 220141 Minsk, Belarus |
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| Abstract: | A short and efficient procedure has been developed for the synthesis of C,D-cis coupled steroid and d-homo steroid skeletons. A Mukaiyama reaction with transfer of the silyl group of the starting silyl enol ether to the enol of the adduct followed by addition of vinyl magnesium bromide to the unprotected carbonyl group leads to adducts which can be cyclized with ZnBr2. The synthesis of functionalized steroid skeletons in overall yields of about 50% in four steps can be achieved in this way. |
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| Keywords: | Mukaiyama-Michael addition homo-steroid synthesis C D-cis steroids carvone |
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