Nhatrangin A: Total Syntheses of the Proposed Structure and Six of Its Diastereoisomers

Author(s)

Dias, Luiz C. ; Polo, Ellen C.

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 82, n. 8, p. 4072-4112, APR 21 2017.
• Web of Science Citations: 6

Abstract

A total synthesis Of the proposed structure of nhatrangin A is described. This strategy relies on two aldol reactions to install the chiral centers at C3/C4 and C3'/C4', a lithium-mediated coupling between an advanced intermediate alkyne and a Weinreb amide to complete the C1-C13 alkyl scaffold, and a Yamaguchi esterification to set the side chain. Discrepancies in the spectroscopic data between synthetic and natural nhatrangins led us to synthesize six more diastereoisomers of the proposed structure of nhatrangin A. (AU)

• FAPESP's process: 11/06722-2 - Total synthesis of nhatrangins A and B
• Grantee: Ellen Christine Polo
• 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