Stereloselective synthesis of methyl 7-dihydro-trioxacarcinoside B
Stereloselective synthesis of methyl 7-dihydro-trioxacarcinoside B
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DOI：
10.1021/ol702078t
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发表时间：
2007-11-08
期刊：
影响因子：
5.2
通讯作者：
Koert, Ulrich
中科院分区：
文献类型：
--
作者：
Konig, Christian M.;Harms, Klaus;Koert, Ulrich
7-二氢三钙糖B是由喹环类化合物衍生的一种支链辛糖，已实现了立体选择性合成。贝利斯-希尔曼加合物的生物催化拆分和随后的闭环复分解被用来组装分子框架。随后的关键步骤是高立体选择性的环氧化，以及用烯丙醇和HClO4以保护形式引入C(3)-OH基团的环氧化物的区域和立体选择性开环。7-二氢三钙糖B可转化为相应的1，7-脱水糖。
A stereoselective synthesis of 7-dihydro-triocacarcinose B, a branched octose from the quinocyclines, has been achieved. The biocatalytic resolution of a Baylis - Hillman adduct and a subsequent ring-closing metathesis were used to assemble the molecular framework. Subsequent key steps were a highly stereoselective epoxidation and a regio- and stereoselective opening of the epoxide by allyl alcohol and HClO4 to introduce the C(3)-OH group in protected form. The 7-dihydro-triocacarcinose B could be converted into the corresponding 1,7-anhydrosugar.