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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.)

Coibacins A and B: Total Synthesis and Stereochemical Revision

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Author(s):
Carneiro, Vania M. T. [1] ; Avila, Carolina M. [1] ; Balunas, Marcy J. [2] ; Gerwick, William H. [3, 4] ; Pilli, Ronaldo A. [1]
Total Authors: 5
Affiliation:
[1] Univ Campinas Unicamp, Inst Chem, BR-13084971 Campinas, SP - Brazil
[2] Univ Connecticut, Dept Pharmaceut Sci, Div Med Chem, Storrs, CT 06269 - USA
[3] Univ Calif San Diego, Skaggs Sch Pharm & Pharmaceut Sci, La Jolla, CA 92093 - USA
[4] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 - USA
Total Affiliations: 4
Document type: Journal article
Source: Journal of Organic Chemistry; v. 79, n. 2, p. 630-642, JAN 17 2014.
Web of Science Citations: 17
Abstract

The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent anti-inflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A. (AU)

FAPESP's process: 11/00457-5 - Synthesis of Dihydropyranones, evaluation of the inhibitory activity of CDC25 and cytotoxicity in tumor cells and structural studies
Grantee:Vânia Maria Teixeira Carneiro
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 09/51602-5 - Chemical biology: new natural and synthetic molecular targets against cancer, structural studies, biological evaluation and mode of action
Grantee:Ronaldo Aloise Pilli
Support Opportunities: Research Projects - Thematic Grants
FAPESP's process: 10/08673-6 - Studies toward the Synthesis of Analogues of Fostriecin and Total Synthesis and Structural Elucidation of Coibacinas A and B
Grantee:Carolina Martins Avila de Sant'Ana
Support Opportunities: Scholarships in Brazil - Doctorate