A step-economical divergent approach to isoflavenes based on Suzuki-Miyaura cross coupling of a 3-boryl-2H-chromene with aryl bromides: application to total synthesis of isoflavonoid natural products.

Biosci Biotechnol Biochem

Department of Applied Chemistry in Bioscience, Graduate School of Agricultural Science, Kobe University, 1-1 Rokkodai, Nada, Kobe, Japan.

Published: August 2023

We present a step-economical divergent synthetic approach for isoflavene derivatives using the Suzuki-Miyaura cross coupling of a 3-boryl-2H-chromene and three aryl bromides. 3-Boryl-2H-chromene, which is not a well-explored species, was prepared via Miyaura-Ishiyama borylation of a 3-chloro-2H-chromene obtained through a Claisen rearrangement cyclization cascade reaction. Further conversion of the cross-coupling products, three isoflavene derivatives, afforded three isoflavonoid natural products with one or two additional reaction steps.

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http://dx.doi.org/10.1093/bbb/zbad076DOI Listing

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