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Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition

Abstract:
The chemo- and enantioselective reduction of ethyl 4-chloroacetoacetate and the diastereoselective conjugate addition of enantiopure lithium N-benzyl-N-(α-methylbenzyl)amide to an α,β-unsaturated ester have been used as the key steps in the total asymmetric syntheses of (+)-negamycin (in 13 steps and 24% overall yield), (+)-3-epi-negamycin (in 13 steps and 10% overall yield) and sperabillin C (in 17 steps and 13% overall yield) from commercially available starting materials. © 2010 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Publisher copy:
10.1016/j.tet.2010.10.067

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
More by this author
Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
TETRAHEDRON
Volume:
67
Issue:
1
Pages:
216-227
Publication date:
2011-01-07
DOI:
ISSN:
0040-4020
Source identifiers:
118082
Language:
English
Keywords:
Pubs id:
pubs:118082
UUID:
uuid:6a432f04-834c-4e86-9583-e3e6a754a75c
Local pid:
pubs:118082
Deposit date:
2012-12-19

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