Synthesis of marine brominated alkaloid amathamide F: a palladium-catalyzed enamide synthesis

Saeed, A and Choudhury, S and Khan, Faiz Ahmed (2015) Synthesis of marine brominated alkaloid amathamide F: a palladium-catalyzed enamide synthesis. Tetrahedron, 71 (24). pp. 4192-4202. ISSN 0040-4020

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Abstract

Synthesis of brominated marine natural product amathamide F is described. Various strategies to construct the enamide functionality required for its synthesis have been explored. Finally, we succeeded in constructing the enamide moiety under a palladium-catalyzed condition. Facile transformation of 2,3,4-tribromo-5-methoxybenzaldehyde to the reported structure of amathamide F involved initial one-carbon-elongation of the aldehyde group followed by its conversion to corresponding enol acetate derivative prior to crucial Pd(II)-catalyzed cross-coupling with (S)-1-methylpyrrolidine-2-carboxamide. However, due to nonconformity of its NMR spectral data to that of the reported natural isolate, we have confirmed its actual structure through a synthesis.

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IITH Creators:	IITH Creators ORCiD Khan, Faiz Ahmed UNSPECIFIED
Item Type:	Article
Uncontrolled Keywords:	Alkaloids; Amathamides; Natural products; Palladium catalysis; Structure revision
Subjects:	Chemistry
Divisions:	Department of Chemistry
Depositing User:	Team Library
Date Deposited:	03 Jun 2015 10:43
Last Modified:	21 Sep 2017 06:29
URI:	http://raiithold.iith.ac.in/id/eprint/1555
Publisher URL:	https://doi.org/10.1016/j.tet.2015.04.091
OA policy:	http://www.sherpa.ac.uk/romeo/issn/0040-4020/
Related URLs:	Google Scholar

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