Toward the synthesis of the hypoxia selective anticancer agent BE-43547 A2
- 22 October 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 19 (45), 9833-9839
- https://doi.org/10.1039/d1ob01824h
Abstract
A short and enantioselective synthesis of 19-epi-BE-43547 A2 chiral framework has been achieved in 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. Efficient protocol for Z to E isomerization of olefin was developed using novel UV flow reactor. In addition, an unprecedented oxygen mediated hydroboration, as well as Krapcho de-carboxylation of β-keto lactone were observed.Funding Information
- University Grants Commission
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