A novel synthetic approach to (20R)- and (20S)-21-hydroxy steroids. Synthesis of a marine sterol 21-hydroxycholesterol

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• 作者：Hanna Koenig^a ; Iwona Skiera^a ; Krzysztof B&#x142 ; aszczyk^a ; Zdzis&#x142 ; aw Paryzek ; ^a ; ^{zparyzek@amu.edu.pl}
• 关键词：Natural product ; Synthesis ; Marine sterol ; Side chain
• 刊名：Steroids
• 出版年：2011
• 出版时间：April 2011
• 年：2011
• 卷：76
• 期：5
• 页码：517-523
• 全文大小：504 K

文摘

A short and efficient synthesis of steroid synthons, di(tert-butyldimethylsilyl) ethers of 3,21-dihydroxy-24-nor-chol-5-en-23-al (8 and 10) and of ethyl 3,21-dihydroxy-25-homo-chola-5,23-dien-25-oate (9 and 11), having natural (20R) and unnatural (20S) configuration from 3β-(tert-butyldimethylsilyloxy)-14α,20ξ-card-5-enolide (2) is reported. Further elongation of the side chain of these synthons provides a new method for the synthesis of (20R) and (20S)-21-hydroxy steroids. The utility of the method was exemplified by the synthesis of a natural marine sterol – 21-hydroxycholesterol (18).