A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide
- 作者：Xiang Zhou ; Wen-Jun Liu ; Jian-Liang Ye ; Pei-Qiang Huang
- 关键词：Azasugars ; DAB 1 ; LAB 1 ; 6-Deoxy-DMDP ; epi-Radicamine B ; Alkaloids ; Pyrrolidine ; Hydroxymethylation ; Diastereoselective synthesis
- 刊名：Tetrahedron
- 出版年：2007
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：2 July 2007
- 卷：63
- 期：27
- 页码：6346-6357
- 文件大小：577 K
摘要
A highly diastereoselective synthesis of enantio-enriched all trans-3,4-dibenzyloxyl-5-benzyloxymethyl-2-pyrrolidinone 13a was developed based on SmI2-mediated benzyloxymethylation of O,O′-dibenzyltartarimide. The versatility of 13a and its antipode as the key building blocks for the asymmetric synthesis of pyrrolidine azasugars and homoazasugars has been demonstrated by elaborating them into naturally occurring DAB 1 (1), LAB 1 (2), N-hydroxyethyl-DAB 1 (4), 6-deoxy-DMDP 7, and 5-epi-radicamine B 36 as well as the reductive ring-opening product 35.