A concise total synthesis of (+/-)-1-epiaustraline

Timothy J Donohoe; Herman O Sintim

doi:10.1021/ol049397s

A concise total synthesis of (+/-)-1-epiaustraline

Org Lett. 2004 Jun 10;6(12):2003-6. doi: 10.1021/ol049397s.

Authors

Timothy J Donohoe¹, Herman O Sintim

Affiliation

¹ Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. timothy.donohue@chem.ox.ac.uk

PMID: 15176804
DOI: 10.1021/ol049397s

Abstract

[reaction: see text] A concise total synthesis of 1-epiaustraline 3 is described that utilizes a diastereoselective Birch reduction of an electron-deficient pyrrole and a chelation-controlled vinyl Grignard addition to an aldehyde to introduce the C7 stereocenter. The C1 and C2 stereocenters were set through an OsO(4)-catalyzed dihydroxylation.

Publication types

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

MeSH terms

Catalysis
Molecular Conformation
Osmium Tetroxide / chemistry
Pyrrolizidine Alkaloids / chemical synthesis*
Stereoisomerism

Substances

Pyrrolizidine Alkaloids
epiaustraline
Osmium Tetroxide