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

Ramagonolla Kranthikumar

doi:10.1039/D1OB01824H

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

Ramagonolla Kranthikumar

*^ab

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* Corresponding authors

^a Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India
E-mail: Kranthiramagonolla@fas.harvard.edu

^b Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA

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.

This article is part of the themed collection: Total synthesis in OBC

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Article information

DOI: https://doi.org/10.1039/D1OB01824H
Article type: Communication
Submitted: 15 sept. 2021
Accepted: 22 oct. 2021
First published: 22 oct. 2021

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

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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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Organic & Biomolecular Chemistry