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

TETRAHEDRON

卷:71

Article

Ahmad, Saeed¹  Choudhury, Sumit¹  Khan, Faiz Ahmed² 

[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India

[2] Indian Inst Technol Hyderabad, Dept Chem, Ordnance Factory Estate, Yeddumailaram 502205, India

关键词: Alkaloids;    Amathamides;    Natural products;    Palladium catalysis;    Structure revision;   

DOI  :  10.1016/j.tet.2015.04.091

来源: Elsevier

【 摘 要 】

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 onecarbon-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. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

Free