Synthesis of Papulacandin D

S. E. Denmark; C. S. Regens; T. Kobayashi

doi:10.1055/s-2007-968718

Synfacts, Table of Contents

Synfacts 2007(8): 0781-0781
DOI: 10.1055/s-2007-968718

Synthesis of Natural Products and Potential Drugs

Synthesis of Papulacandin D

Contributor(s):Philip Kocienski

S. E. Denmark*, C. S. Regens, T. Kobayashi
University of Illinois at Urbana-Champaign, USA
Total Synthesis of Papulacandin D
J. Am. Chem. Soc. 2007, 129: 2774-2776

Abstract

Full Text

PDF Download

Key words

silanol cross-coupling - cross metathesis - allylation - C-aryl glycosides - palladium

Significance

Papulacandin D is a potent antifungal agent. Highlights of the Denmark synthesis include (a) a Pd-catalyzed coupling of iodoarene C with the silanol B to generate the 2-arylglycal D and (b) the asymmetric allylation of aldehyde F mediated by the bisphosphoramide G (S. E. Denmark et al. J. Org. Chem. 2006, 71, 1513; J. Org. Chem. 2006, 71, 1523).

Comment

The only previous synthesis of papulacandin D used the nucleophilic addition of an aryllithium to a D-gluconolactone derivative to construct the C-aryl glycoside bond: A. G. M. Barrett, M. Peña, J. A. Willardsen J. Org. Chem. 1996, 61, 1082.

Figures