Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis

Authors

Stephen G. Pyne, University of WollongongFollow
Christopher Au, University of WollongongFollow
Andrew S. Davis, University of Wollongong
Ian R. Morgan, University of WollongongFollow
Thunwadee Ritthiwigrom, University of WollongongFollow
Arife Yazici, University of WollongongFollow

RIS ID

25501

Publication Details

Pyne, S. G., Au, C. W. G.., Davis, A. S., Morgan, I. R., Ritthiwigrom, T. & Yazici, A. (2008). Exploiting the borono-Mannich reaction in bioactive alkaloid synthesis. Pure and Applied Chemistry, 80 (4), 751-762.

Abstract

We have demonstrated that the borono-Mannich reaction is a versatile and efficient reaction for the diastereoselective preparation of chiral 1,2-amino alcohols. These Mannich products are valuable starting materials as shown in this report by the synthesis of bioactive polyhydroxylated pyrrolizidine and indolizidine alkaloids. Initial studies, directed at the more complex Stemona alkaloids, using the borono-Mannich reaction on cyclic N-acyliminium ions are encouraging as demonstrated by the synthesis of the pyrido[1,2-a]azepine core structure of stemocurtisinol.