Synthesis of 6,6'-binaphthopyran-2-one natural products: pigmentosin A, talaroderxines A and B
Charles I Grove1, Michael J Di Maso, Firoz A Jaipuri
1Department of Chemistry, One Shields Avenue, University of California, Davis, California 95616, USA.
Abstract:
Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.
More Related Videos
Related Concept Videos
Biosynthesis of Nucleic Acids
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
Thermal and Photochemical Electrocyclic Reactions: Overview

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
