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Flexibility in the partial reduction of 2,5-disubstituted pyrroles: application to the synthesis of DMDP.

Abstract:
[reaction: see text] The partial reduction of electron-deficient 2,5-disubstituted pyrroles has been developed into a flexible procedure that gives control of relative stereochemistry by variation of the reduction conditions. After the reaction, the pyrroline products were dihydroxylated at C-3,4 to give either the cis or trans isomers; this flexibility means that a variety of polyhydroxylated pyrrolidines can be prepared in a short sequence. Finally, this method was applied to a synthesis of the naturally occurring glycosidase inhibitor DMDP.
Publication status:
Published

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Publisher copy:
10.1021/ol027504h

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic letters
Volume:
5
Issue:
7
Pages:
999-1002
Publication date:
2003-04-05
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
URN:
uuid:c362dcd1-c442-4ec8-92eb-05bc002e96e1
Source identifiers:
32336
Local pid:
pubs:32336

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