A versatile approach to pyrrolidine azasugars and homoazasugars based on a highly diastereoselective reductive benzyloxymethylation of protected tartarimide

作者：Zhou, Xiang; Liu, Wen-Jun; Ye, Jian-Liang; Huang, Pei-Qiang^*

来源：Tetrahedron, 2007, 63(27): 6346-6357.

DOI：10.1016/j.tet.2007.02.087

• ALPHA-METHOXY AMIDES
• N-ACYLIMINIUM IONS
• STEREOSELECTIVE-SYNTHESIS
• ASYMMETRIC-SYNTHESIS
• ENANTIOSELECTIVE SYNTHESIS
• GLUCOSIDASE INHIBITOR
• AMINO-ACIDS
• EFFICIENT SYNTHESIS
• OXIDATIVE REMOVAL
• ORGANIC-SYNTHESIS

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.

• 出版日期2007-7-2
• 单位厦门大学