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 sept. 2021
Accepted
22 oct. 2021
First published
22 oct. 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

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