Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine

Authors

Xuan Duc Dau, University of WollongongFollow
Anthony C. Willis, Australian National University
Stephen G. Pyne, University of WollongongFollow

RIS ID

104246

Publication Details

Dau, X., Willis, A. C. & Pyne, S. G. (2015). Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine. European Journal of Organic Chemistry, 2015 (35), 7682-7694.

Abstract

The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C-3a-C-11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A-ring.

Additional Grant Number

http://purl.org/au-research/grants/ARC/DP130101968