Regiospecific and stereoselective syntheses of (+/-) morphine, codeine, and thebaine via a highly stereocontrolled intramolecular 4 + 2 cycloaddition leading to a phenanthrofuran system

Gilbert Stork; Ayako Yamashita; Julian Adams; Gary R Schulte; Richard Chesworth; Yoji Miyazaki; Jay J Farmer

doi:10.1021/ja9038505

Regiospecific and stereoselective syntheses of (+/-) morphine, codeine, and thebaine via a highly stereocontrolled intramolecular 4 + 2 cycloaddition leading to a phenanthrofuran system

J Am Chem Soc. 2009 Aug 19;131(32):11402-6. doi: 10.1021/ja9038505.

Authors

Gilbert Stork¹, Ayako Yamashita, Julian Adams, Gary R Schulte, Richard Chesworth, Yoji Miyazaki, Jay J Farmer

Affiliation

¹ Department of Chemistry, Columbia University, New York, New York, USA. [email protected]

PMID: 19624126
DOI: 10.1021/ja9038505

Abstract

Total syntheses of the morphine alkaloids are described that use a direct stereoselective formation of the phenanthrofuran system via an intramolecular 4 + 2 cycloaddition of a diene tethered to the 4-position of a 7-methoxybenzofuran-3-carboxylic acid ester.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Codeine / chemical synthesis*
Molecular Structure
Morphine / chemical synthesis*
Stereoisomerism
Thebaine / chemical synthesis*

Substances

Thebaine
Morphine
Codeine