Epoxide opening-induced tandem 8-azabicyclo[3.2.1]octane to 6-azabicyclo[3.2.1]octane rearrangement-iminium allylation: synthesis of (+/-)-peduncularine

David M Hodgson; Ruth E Shelton; Thomas A Moss; Mouloud Dekhane

doi:10.1021/ol100943j

Epoxide opening-induced tandem 8-azabicyclo[3.2.1]octane to 6-azabicyclo[3.2.1]octane rearrangement-iminium allylation: synthesis of (+/-)-peduncularine

Org Lett. 2010 Jun 18;12(12):2834-7. doi: 10.1021/ol100943j.

Authors

David M Hodgson¹, Ruth E Shelton, Thomas A Moss, Mouloud Dekhane

Affiliation

¹ Department of Chemistry, University of Oxford, Chemistry Research Laboratory, UK. david.hodgson@chem.ox.ac.uk

PMID: 20469871
DOI: 10.1021/ol100943j

Abstract

An efficient Lewis acid induced nitrogen-driven rearrangement iminium-trapping cascade from an epoxytropinone 3 gives a 7-allylated 6-azabicyclo[3.2.1]octan-3-one 2, which is converted into the alkaloid (+/-)-peduncularine (1).

Publication types

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

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Azabicyclo Compounds / chemistry*
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Molecular Structure
Octanes / chemistry*
Stereoisomerism

Substances

Alkaloids
Azabicyclo Compounds
Indole Alkaloids
Octanes
peduncularine