- 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
- Publisher copy:
- 10.1016/j.tet.2010.10.067
-
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- Journal:
- TETRAHEDRON
- Volume:
- 67
- Issue:
- 1
- Pages:
- 216-227
- Publication date:
- 2011-01-07
- DOI:
- ISSN:
-
0040-4020
- URN:
-
uuid:6a432f04-834c-4e86-9583-e3e6a754a75c
- Source identifiers:
-
118082
- Local pid:
- pubs:118082
- Language:
- English
- Keywords:
- Copyright date:
- 2011
Journal article
Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition
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