Issue 45, 2022

Total synthesis of the antibacterial polyketide natural product thailandamide lactone

Abstract

Stereoselective total synthesis of the structurally intriguing polyketide natural product thailandamide lactone was accomplished, and done so using a convergent approach for the first time to the best of our knowledge. The key features of this synthesis included use of a Crimmins acetate aldol reaction, Evans methylation, Urpi acetal aldol reaction, Sharpless asymmetric epoxidation and subsequent γ-lactonization for the installation of six asymmetric centers and the use of the Negishi reaction, Julia-Kocienski olefination, cross metathesis, HWE olefination and intermolecular Heck coupling for construction of a variety of unsaturated linkages. Pd(I)-based Heck coupling was introduced, for the first time to the best of our knowledge, quite efficiently to couple the major eastern and sensitive western segments of the molecule. The antibacterial activity of thailandamide lactone was also evaluated.

Graphical abstract: Total synthesis of the antibacterial polyketide natural product thailandamide lactone

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Aug. 2022
Accepted
20 Okt. 2022
First published
21 Okt. 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 13403-13408

Total synthesis of the antibacterial polyketide natural product thailandamide lactone

H. Sharma, J. Mondal, A. K. Ghosh, R. R. Pal and R. K. Goswami, Chem. Sci., 2022, 13, 13403 DOI: 10.1039/D2SC04727F

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