De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation
De novo asymmetric syntheses of SL0101 and its analogues via a palladium-catalyzed glycosylation
复制标题
DOI：
10.1021/ol062076r
复制
发表时间：
2006-10-26
期刊：
影响因子：
5.2
通讯作者：
O'Doherty, George A.
中科院分区：
文献类型：
--
作者：
Shan, Mingde;O'Doherty, George A.
天然山奈酚糖苷SL0101(1a)及其类似物1b-e及其对映体的对映选择性合成经7-10步完成。这些路线依赖于钯催化的非对映选择性糖基化、酮还原和二羟基化来引入鼠李糖立体化学。这些山奈酚糖苷糖基的不对称性源于酰基呋喃的Noyori还原。在碱性条件下，乙酰基从轴向(C-2)向赤道位置(C-3)移动。
The enantioselective syntheses of naturally occurring kaempferol glycoside SL0101 (1a) and its analogues 1b-e, as well as their enantiomers, have been achieved in 7-10 steps. The routes rely upon a diastereoselective palladium-catalyzed glycosylation, ketone reduction, and dihydroxylation to introduce the rhamno-stereochemistry. The asymmetry of the sugar moiety of these kaempferol glycosides was derived from Noyori reduction of an acylfuran. An acetyl group shift from an axial (C-2) to equatorial position (C-3) under basic conditions was also described.