title: Nhatrangin A: Total Syntheses of the Proposed Structure and Six of Its Diastereoisomers.
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.
authors.affiliation: Institute of Chemistry, University of Campinas , 13083-970, C.P. 6154, Campinas, SP, Brazil.
authors.forename: Luiz C
authors.identifier: 0000-0003-0628-9928
authors.initials: LC
authors.lastname: Dias
authors.affiliation: Institute of Chemistry, University of Campinas , 13083-970, C.P. 6154, Campinas, SP, Brazil.
authors.forename: Ellen C
authors.initials: EC
authors.lastname: Polo
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D008235:Lyngbya Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D066244:Proton Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D008235:Lyngbya Toxins; C549735:nhatrangin A