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An oxidation and ring contraction approach to the synthesis of (+/-)-1-deoxynojirimycin and (+/-)-1-deoxyaltronojirimycin.

Abstract:
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.
Publication status:
Published

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Publisher copy:
10.1021/ol902533b

Authors


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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Roberts, PM More by this author
Russell, AJ More by this author
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Journal:
Organic letters
Volume:
12
Issue:
1
Pages:
136-139
Publication date:
2010-01-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:c17944b6-880a-43fa-81c3-04b36e1b16a0
Source identifiers:
34998
Local pid:
pubs:34998

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