An Oxidation and Ring Contraction Approach to the Synthesis of (+/-)-1-Deoxynojirimycin and (+/-)-1-Deoxyaltronojirimycin

作者：Bagal Sharan K; Davies Stephen G^*; Lee James A; Roberts Paul M; Russell Angela J; Scott Philip M; Thomson James E

来源：Organic Letters, 2010, 12(1): 136-139.

DOI：10.1021/ol902533b

A reaction sequence involving the chemoselective olefinic oxidation of N(1)-benzyl-2,7-dihydro-1H-azepine with m-CPBA in the presence of HBF(4) and BnOH followed by ring contraction facilitates the stereoselective preparation of either of the epoxide diastereoisomers of (2RS,3SR)-N(1)-benzyl-2-chloromethyl-3-benzyloxy-4,5-epoxypiperidine by simple modification of the reaction conditions. Epoxide ring opening, functional group interconversion, and deprotection allow the synthesis of (+/-)-1-deoxynojirimycin and (+/-)-1-deoxyaltronojirimycin.

• 出版日期2010-1-1