Issue 1, 2016

Total synthesis and preliminary SAR study of (±)-merochlorins A and B

Abstract

A modular synthesis of merochlorins A and B, two naturally occurring antibiotics, has been achieved concisely from readily available building blocks in 4–6 steps. The key steps include the bio-inspired tandem phenol oxidative dearomatization/[5 + 2] and [3 + 2] cycloadditions to construct the tricyclic cores of the targets, and the intermolecular Diels–Alder reaction followed by dehydrogenative aromatization to assemble the remaining aromatic units. The antibacterial activities of merochlorins A, B and some advanced synthetic intermediates were also evaluated, which provided valuable information on the structure–activity relationship (SAR) of this class of new antibiotics.

Graphical abstract: Total synthesis and preliminary SAR study of (±)-merochlorins A and B

Supplementary files

Article information

Article type
Paper
Submitted
18 Sep 2015
Accepted
13 Oct 2015
First published
14 Oct 2015

Org. Biomol. Chem., 2016,14, 198-205

Author version available

Total synthesis and preliminary SAR study of (±)-merochlorins A and B

H. Yang, X. Liu, Q. Li, L. Li, J. Zhang and Y. Tang, Org. Biomol. Chem., 2016, 14, 198 DOI: 10.1039/C5OB01946J

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