An oxidation and ring contraction approach to the synthesis of (+/-)-1-deoxynojirimycin and (+/-)-1-deoxyaltronojirimycin.
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.
Bagal
Sharan K
SK
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
Davies
Stephen G
SG
Lee
James A
JA
Roberts
Paul M
PM
Russell
Angela J
AJ
Scott
Philip M
PM
Thomson
James E
JE
D017485:1-Deoxynojirimycin / Q000138:chemical synthesis* / Q000737:chemistry; D001381:Azepines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D001381:Azepines; D017485:1-Deoxynojirimycin