通过发散的从头不对称方法合成几种密穗岩黄芪苷和密穗岩黄芪苷天然产物。
Synthesis of several cleistrioside and cleistetroside natural products via a divergent de novo asymmetric approach.
机构信息
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
出版信息
Org Lett. 2010 Dec 3;12(23):5466-9. doi: 10.1021/ol1023344. Epub 2010 Nov 1.
Abstract
The de novo asymmetric syntheses of several partially acylated dodecanyl tri- and tetra-rhamnoside natural products (cleistriosides-5 and 6 and cleistetrosides-2 to 7) have been achieved (19-24 steps). The divergent route requires the use of three or less protecting groups. The asymmetry was derived via Noyori reduction of an acylfuran. The rhamno-stereochemistry was installed by a diastereoselective palladium-catalyzed glycosylation, ketone reduction and dihydroxylation.
摘要
已实现几种部分酰化十二烷基三糖苷和四糖苷天然产物（cleistriosides-5 和 6 及 cleistetrosides-2 至 7）的从头不对称合成（19-24 步）。发散途径需要使用三个或更少的保护基。不对称性是通过酰基呋喃的 Noyori 还原得到的。通过非对映选择性钯催化糖苷化、酮还原和二羟基化来安装鼠李糖立体化学。
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