斯特罗伐他汀 C、E 和 F 的合成。
Synthesis of Strophasterols C, E, and F.
机构信息
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science , Tohoku University , 468-1 Aramaki Aza-Aoba , Aoba-ku, Sendai 980-8572 , Japan.
出版信息
Org Lett. 2020 Feb 21;22(4):1311-1315. doi: 10.1021/acs.orglett.9b04628. Epub 2020 Jan 29.
The synthesis of strophasterols C, E, and F has been accomplished from a 14,15-secoergostane derivative via a 1,3-dipolar cycloaddition of a nitrile oxide intermediate to simultaneously install an isolated cyclopentane ring and a C23 oxygen functionality in a diastereoselective manner and a regio- and diastereoselective selenohydroxylation of an olefinic intermediate under thermodynamic conditions. This synthesis also enabled the stereochemical confirmation of strophasterol C.
已从 14,15-降甾烷衍生物合成了甾醇 C、E 和 F，方法是通过腈氧化物中间体的 1,3-偶极环加成反应，以非对映选择性的方式同时安装一个孤立的环戊烷环和 C23 氧官能团，并在热力学条件下对烯烃中间体进行区域和非对映选择性硒羟基化。该合成还使甾醇 C 的立体化学结构得到确认。
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