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A new approach toward the synthesis of C,D-cis coupled steroid and C,D-cis coupled d-homosteroid skeletons

✍ Scribed by Svetlana Dratch; Tanya Charnikhova; Florence C.E Sarabèr; Ben J.M Jansen; Aede de Groot

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
221 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

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 ZnBr 2 . 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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