Xiang Zhou, Wen-Jun Liu, Jian-Liang Ye
Jul 2, 2007
Citations
0
Influential Citations
44
Citations
Journal
Tetrahedron
Abstract
Abstract A highly diastereoselective synthesis of enantio-enriched all trans -3,4-dibenzyloxyl-5-benzyloxymethyl-2-pyrrolidinone 13a was developed based on SmI 2 -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 .