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Ireland–Claisen rearrangement of steroidal Δ23-22-alcohols: an application to Δ22,25-24-alkyl steroid synthesis

✍ Scribed by Vladimir A. Khripach; Vladimir N. Zhabinskii; Olga V. Konstantinova; Natalya B. Khripach

Book ID: 104210561
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 108 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00900-x

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✦ Synopsis

A new method for the preparation of a 1,4-diene system in the steroid side chain, providing the possibility of stereocontrol at C-3 has been described. Its usefulness has been examined for Á 22,25 -24-alkyl steroid synthesis. The proposed approach is based on the Ireland±Claisen rearrangement of Á 23 -22-alcohols followed by C-25 silylation of the formed ester and Peterson ole®nation as the ®nal step.

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