Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland.
Steroids. 2011 Apr;76(5):517-23. doi: 10.1016/j.steroids.2011.01.010. Epub 2011 Feb 3.
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).
甾体合成子的短捷高效合成——3β-（叔丁基二甲基硅氧基）-14α，20ξ-卡-5-烯-2-醇内酯（2）的 3，21-二羟基-24-降胆-5-烯-23-醛的二（叔丁基二甲基硅基）醚（8 和 10）和乙基 3，21-二羟基-25-高同型胆-5，23-二烯-25-酸酯（9 和 11）的合成，其中包括天然（20R）和非天然（20S）构型。这些合成子的侧链进一步延长，为（20R）和（20S）-21-羟基甾体的合成提供了一种新方法。该方法的实用性通过天然海洋甾醇-21-羟基胆固醇（18）的合成得到了例证。
