Journal
TETRAHEDRON LETTERS
Volume 53, Issue 26, Pages 3250-3253Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.04.042
Keywords
Manzacidin B; [Bis(N-tert-butylsalicyliden-iminate)]copper catalyst; Isocyanoacetate aldol reaction; Oppolzer's camphorsultam
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Funding
- Japan Society for the Promotion of Science (JSPS) [16201045, 16073214, 18510191, 19201045]
- Ministry of Education, Culture, Sports, Science, and Technology, Japan
- Grants-in-Aid for Scientific Research [16201045, 21310145, 19201045, 18510191, 16073214] Funding Source: KAKEN
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The highly diastereoselective synthesis of the marine natural product, (-)-manzacidin B, is described. A novel copper-catalyzed aldol reaction of the alpha-methylserine-derived aldehyde with an isocyanoacetate possessing (1R)-camphorsultam as the chiral auxiliary proceeded in a highly diastereoselective manner to give the (4R,5R,6R)-adduct, which was converted into manzacidin B in a few steps. (C) 2012 Elsevier Ltd. All rights reserved.
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