Cascade Transformation of the Ansamycin Benzoquinone Core into Benzoxazole Influencing Anticancer Activity and Selectivity

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2023 Jun 5

PMID 37276434

Authors

Natalia Skrzypczak

Krystian Pyta

Wiktor Bohusz

Aleksandra Lesniewska

Maria Gdaniec

Piotr Ruszkowski

Wojciech Schilf

Franz Bartl

Piotr Przybylski

Affiliations

Soon will be listed here.

Abstract

The metal-free cascade transformation of geldanamycin benzoquinone core is proposed at relatively mild conditions. This approach yields new benzoxazole ansamycin antibiotics and enables their functionalization in an atom-economic manner, irrespective of the type of amine used. The analysis of the heterocyclization course reveals the dependence of its rate on the nature of the -substituent within the benzylamine moiety (EDG/EWG) and the strength of the base. The reduction of the ansamycin core enables an increase in anticancer potency and selectivity.

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