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

A short and enantioselective synthesis of the 19-epi-BE-43547 A(2) 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 beta-keto lactone were observed.

Automated summary

This study achieved a short and enantioselective synthesis of the 19-epi-BE-43547 A(2) chiral framework in a high yield. The synthetic strategy involved innovative methods such as Julia-Kocienski olefination and Z to E isomerization of olefin using a novel UV flow reactor. Additionally, unprecedented oxygen mediated hydroboration and the Krapcho decarboxylation of beta-keto lactone were observed.