Issue 7, 2024

Stereoselective synthesis of thailandamide A methyl ester

Abstract

A convergent strategy for the stereoselective synthesis of the methyl ester of the structurally challenging and highly labile antibacterial polyene polyketide natural product thailandamide A has been developed. The key steps include the Zincke aldehyde reaction, Stille cross coupling, Negishi reaction, Julia–Kocienski olefination, cross metathesis, and the less explored Pd(I)-based Heck coupling to access different unsaturation bonds. Additionally, Urpi acetal aldol, Evans methylation, and Crimmins acetate aldol reactions were employed to construct four out of six asymmetric centers of the molecule.

Graphical abstract: Stereoselective synthesis of thailandamide A methyl ester

Supplementary files

Article information

Article type
Paper
Submitted
26 Dec. 2023
Accepted
18 Janv. 2024
First published
19 Janv. 2024

Org. Biomol. Chem., 2024,22, 1409-1419

Stereoselective synthesis of thailandamide A methyl ester

H. Sharma, S. Ganguly, M. H. Sahana and R. K. Goswami, Org. Biomol. Chem., 2024, 22, 1409 DOI: 10.1039/D3OB02107F

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