| Full text | |
| 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 |