Total Synthesis of (±)-Spiroaxillarone A via a Reversible Sulfa-Michael Addition.

Org Lett

State Key Laboratory and Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

Published: February 2022

AI Article Synopsis

  • A bioinspired approach was developed for the total synthesis of spiroaxillarone A, a compound showing strong antimalarial effects against resistant strains (IC = 2.32 μM).
  • The synthesis involves important reactions such as an intermolecular ethanethiol Michael addition and a -quinone Michael addition, followed by a β-ethanethiol elimination.
  • This synthetic method not only achieves the target compound but also suggests a potential biosynthetic pathway for spiroaxillarone A.

Article Abstract

A bioinspired strategy is described for the total synthesis of spiroaxillarone A, which exhibited significant antimalarial activity against resistant (IC = 2.32 μM). The key steps include an intermolecular ethanethiol Michael addition, -quinone Michael addition, and subsequent β-ethanethiol elimination. This synthetic sequence provides a potential biosynthetic pathway of spiroaxillarone A.

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Source
http://dx.doi.org/10.1021/acs.orglett.1c04282DOI Listing

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