Total Synthesis of (-)-Marinisporolide C - BV FAPESP
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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Total Synthesis of (-)-Marinisporolide C

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Author(s):
Dias, Luiz C. ; de Lucca, Emilio C.
Total Authors: 2
Document type: Journal article
Source: Journal of Organic Chemistry; v. 82, n. 6, p. 3019-3045, MAR 17 2017.
Web of Science Citations: 13
Abstract

The first total synthesis of (-)-marinisporolide C is described, which establishes unequivocally the relative and absolute configuration of this oxopolyene macrolide. Key features of this synthesis include a series of highly stereoselective aldol reactions followed by directed reductions to build the polyol domain, a Stile cross-coupling reaction to assemble the polyene, and an infra molecular Horner-Wadsworth-Emmons olefination to forge the macrocyclic ring. Despite the initial approach to marinisporolide A using a Yamaguchi macrolactonization reaction that was unsuccessful due to steric hindrance of the oxygen at the C33 position, we were able to prepare a known derivative of marinisporolide A and consequently confirm its stereochemical assignment. (AU)

FAPESP's process: 11/06721-6 - Total synthesis of marinisporolide A
Grantee:Emílio Carlos de Lucca Júnior
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 12/02230-0 - Total synthesis of bioactive compounds: biological tests and design of new analogs
Grantee:Luiz Carlos Dias
Support Opportunities: Regular Research Grants
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC