通过环间环化反应简洁地合成了苦甜藤定碱。
A concise synthesis of castanospermine by the use of a transannular cyclization.
机构信息
Department of Chemistry, Building 201, Technical University of Denmark, DK-2800 Lyngby, Denmark.
出版信息
J Org Chem. 2009 Nov 20;74(22):8886-9. doi: 10.1021/jo9019495.
PMID:19856948
Abstract
A nine-step synthesis of (+)-castanospermine has been accomplished in 22% overall yield from methyl alpha-D-glucopyranoside. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 6-iodoglucopyranoside, ring-closing olefin metathesis, and strain-release transannular cyclization to afford the indolizidine skeleton of the natural product.
摘要
从甲基 alpha-D-吡喃葡萄糖苷出发，以 22%的总收率完成了 (+)-苦参碱的九步合成。关键转化涉及苄基保护的甲基 6-碘代吡喃葡萄糖苷的锌介导断裂、闭环烯烃复分解以及应变释放的环间环化，以提供天然产物的吲哚里西定骨架。
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