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 dek 2023
Accepted
18 yan 2024
First published
19 yan 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements