Total synthesis and absolute configuration of (-)-berkeleyamide A

Jonathan Sperry; Eric B J Harris; Margaret A Brimble

doi:10.1021/ol902525k

Total synthesis and absolute configuration of (-)-berkeleyamide A

Org Lett. 2010 Feb 5;12(3):420-3. doi: 10.1021/ol902525k.

Authors

Jonathan Sperry¹, Eric B J Harris, Margaret A Brimble

Affiliation

¹ Department of Chemistry, University of Auckland, 23 Symonds Street, Auckland, New Zealand.

PMID: 20030315
DOI: 10.1021/ol902525k

Abstract

A chiral-pool approach to (-)-berkeleyamide A 1 based on a diastereoselective nitrile oxide [3 + 2]-cycloaddition completes the first total synthesis establishing the absolute stereochemistry of the natural product.

Publication types

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

MeSH terms

Biological Products / chemical synthesis*
Biological Products / chemistry*
Catalysis
Cyclization
Molecular Structure
Penicillium / chemistry
Pyrrolidinones / chemical synthesis*
Pyrrolidinones / chemistry*
Stereoisomerism

Substances

Biological Products
Pyrrolidinones
berkeleyamide A