Total synthesis of uniflorine A, casuarine, australine, 3-epi-australine, and 3,7-di-epi-australine from a common precursor

Thunwadee Ritthiwigrom; Anthony C Willis; Stephen G Pyne

doi:10.1021/jo902355p

Total synthesis of uniflorine A, casuarine, australine, 3-epi-australine, and 3,7-di-epi-australine from a common precursor

J Org Chem. 2010 Feb 5;75(3):815-24. doi: 10.1021/jo902355p.

Authors

Thunwadee Ritthiwigrom¹, Anthony C Willis, Stephen G Pyne

Affiliation

¹ School of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia.

PMID: 20028000
DOI: 10.1021/jo902355p

Abstract

A flexible method for the diastereoselective total synthesis of the pyrrolizidine alkaloids uniflorine A, casuarine, australine, and 3-epi-australine and the unnatural epimer 3,7-di-epi-australine from a common chiral 2,5-dihydropyrrole precursor is described.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Catalysis
Indolizines / chemical synthesis*
Indolizines / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Pyrroles / chemical synthesis
Pyrroles / chemistry*
Pyrrolizidine Alkaloids / chemical synthesis*
Pyrrolizidine Alkaloids / chemistry
Stereoisomerism

Substances

Alkaloids
Indolizines
Pyrroles
Pyrrolizidine Alkaloids
casuarine
epiaustraline
uniflorine A
australine