Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products

Abstract

The halenaquinol family of naphthoquinol natural products includes a few closely related polycyclic compounds that feature an activated, electrophilic furan ring. This motif is likely responsible for the rich biological activity attributed to these secondary metabolites. Their interesting structures—related via their electrophilic furan to the biologically important furanosteroids—and their activities prompted significant efforts by organic chemists that resulted in many strategically compelling laboratory syntheses of these targets. These different strategies are compared and contrasted in this Microreview, and the authors’ recent work on the structurally different but biogenetically related natural product exiguaquinol is put into the context of the previous studies on halenaquinol-type targets.

Thieme‐IUPAC‐Preis:A. Li / Springer‐Preis für Heterocyclenchemie: C. D. Vanderwal / IACS‐Preise:X. Hu, A. Corma

“…Vanderwals Gruppe entwickelt Synthesestrategien für komplexe biologisch aktive Naturstoffe, und sie untersucht deren Wirkmechanismen und Biosynthese. In einem Forschungsartikel in der Angewandten Chemie beschrieben sie jüngst Bicyclisierungen, die durch cobaltkatalysierten Wasserstoffatomtransfer ausgelöst werden, und in einem Microreview im European Journal of Organic Chemistry fassten sie Synthesestrategien für Halenachinol‐ und Xestochinol‐Naturstoffe zusammen …”

Thieme–IUPAC Prize:A. Li / Springer Heterocyclic Chemistry Award:C. D. Vanderwal / IACS Awards:X. Hu, A. Corma

“…Research efforts in the Vanderwal group include the development of strategies for the synthesis of complex, bioactive natural products and the interrogation of their biological mechanism of action and biosynthesis. In a recent Research Article in Angewandte Chemie they described bicyclizations that can be induced by cobalt‐catalyzed hydrogen‐atom transfer, and in a Microreview in European Journal of Organic Chemistry they summarized strategies for the synthesis of halenaquinol and xestoquinol natural products …”

Arthur C. Cope Scholar Awards

“…Er entwickelt gemeinsam mit seiner Gruppe kurze Synthesen von komplexen Naturstoffen, die Studien in chemischer Biologie, Medizin oder Biosynthese erleichtern können. In einem Microreview im European Journal of Organic Chemistry hat er die Synthesen der Naturstofffamilien der Halenachinole und Xestochinole diskutiert …”