Issue 45, 2021

Toward the synthesis of the hypoxia selective anticancer agent BE-43547 A2

Abstract

A short and enantioselective synthesis of the 19-epi-BE-43547 A2 chiral framework has been achieved in a high yield. The challenging key C15 tertiary stereocenter was derived from D-glucose. The synthetic strategy involves a Julia–Kocienski olefination to install the lipophilic side chain. An efficient protocol for Z to E isomerization of olefin was developed using a novel UV flow reactor. In addition, an unprecedented oxygen mediated hydroboration and the Krapcho decarboxylation of β-keto lactone were observed.

Graphical abstract: Toward the synthesis of the hypoxia selective anticancer agent BE-43547 A2

Supplementary files

Article information

Article type
Communication
Submitted
15 Sep 2021
Accepted
22 Okt 2021
First published
22 Okt 2021

Org. Biomol. Chem., 2021,19, 9833-9839

Toward the synthesis of the hypoxia selective anticancer agent BE-43547 A2

R. Kranthikumar, Org. Biomol. Chem., 2021, 19, 9833 DOI: 10.1039/D1OB01824H

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