Catalytic enantioselective desymmetrisation as a tool for the synthesis of hodgkinsine and hodgkinsine B

Robert H Snell; Matthew J Durbin; Robert L Woodward; Michael C Willis

doi:10.1002/chem.201203150

Catalytic enantioselective desymmetrisation as a tool for the synthesis of hodgkinsine and hodgkinsine B

Chemistry. 2012 Dec 21;18(52):16754-64. doi: 10.1002/chem.201203150. Epub 2012 Nov 30.

Authors

Robert H Snell¹, Matthew J Durbin, Robert L Woodward, Michael C Willis

Affiliation

¹ Department of Chemistry, University of Oxford, Chemistry Research Laboratory, UK.

PMID: 23203932
DOI: 10.1002/chem.201203150

Abstract

Two palladium-catalysed amination protocols are deployed in the desymmetrisation of the complex dimeric alkaloid meso-chimonanthine. The power of these transformations is showcased in an efficient formal and total synthesis of the natural products hodgkinsine and hodgkinsine B, respectively.

Publication types

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

MeSH terms

Amination
Catalysis
Chemistry Techniques, Synthetic / methods*
Indoles / chemical synthesis*
Indoles / chemistry*
Molecular Structure
Palladium / chemistry
Pyrroles / chemistry*
Stereoisomerism

Substances

Indoles
Pyrroles
hodgkinsine
Palladium
chimonanthine