Synlett 2009(7): 1087-1090  
DOI: 10.1055/s-0028-1088146
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2-epi-Pumiliotoxin C via a Challenging Intramolecular Hydroamination Key Step

Marie-Eve Lebrun, Jennifer Y. Pfeiffer, André M. Beauchemin*
Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie-Curie, Ottawa, ON K1N 6N5, Canada
Fax: +1(613)5625170; e-Mail: andre.beauchemin@uottawa.ca;
Further Information

Publication History

Received 29 January 2009
Publication Date:
20 March 2009 (eFirst)

Abstract

The synthesis of 2-epi-pumiliotoxin C was achieved in ten steps from cyclohexadiene oxide, using a challenging Cope-type hydroamination key step. This cyclization was performed on a mixture of two epimeric hydroxylamines, and a boat transition state is proposed to explain the kinetic preference observed for the cyclization of the epimer leading to N-hydroxy-epipumiliotoxin C.