Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Org Lett. 2010 Dec 3;12(23):5466-9. doi: 10.1021/ol1023344. Epub 2010 Nov 1.
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.
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。
