Synthesis 2015; 47(23): 3711-3716
DOI: 10.1055/s-0035-1560070
paper
© Georg Thieme Verlag Stuttgart · New York

A First Synthesis of Bis(benzoxazole) Natural Products: Nataxazole and AJI9561 via Benzoxazole C–H Activation

Authors

  • Swarnendu Sasmal

    a   Syngenta Biosciences Pvt. Ltd., Santa Monica Works, Corlim, Ilhas, Goa 403110, India   Email: sitaram.pal@syngenta.com
  • Indira Sen

    a   Syngenta Biosciences Pvt. Ltd., Santa Monica Works, Corlim, Ilhas, Goa 403110, India   Email: sitaram.pal@syngenta.com
  • Roger G. Hall

    b   Syngenta Crop Protection, Münchwilen AG, Schaffhauserstrasse, 4332 Stein, Switzerland
  • Sitaram Pal*

    a   Syngenta Biosciences Pvt. Ltd., Santa Monica Works, Corlim, Ilhas, Goa 403110, India   Email: sitaram.pal@syngenta.com
Further Information

Publication History

Received: 25 May 2015

Accepted after revision: 07 July 2015

Publication Date:
18 August 2015 (online)


Graphical Abstract

Abstract

Concise and efficient syntheses of nataxazole and AJI9561 have been accomplished. We also demonstrate a convenient route to obtain the related natural product UK-1. The key step involves C–H activation of a benzoxazole in the presence of ortho-iodoanilides using a copper(I) iodide/Xantphos/palladium(II) acetate system.

Supporting Information