Regiospecific and stereoselective syntheses of (+/-) morphine, codeine, and thebaine via a highly stereocontrolled intramolecular 4 + 2 cycloaddition leading to a phenanthrofuran system.
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.
Stork
Gilbert
G
Department of Chemistry, Columbia University, New York, New York, USA. gjs8@columbia.edu
Yamashita
Ayako
A
Adams
Julian
J
Schulte
Gary R
GR
Chesworth
Richard
R
Miyazaki
Yoji
Y
Farmer
Jay J
JJ
D003061:Codeine / Q000138:chemical synthesis*; D015394:Molecular Structure; D009020:Morphine / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013797:Thebaine / Q000138:chemical synthesis*
D013797:Thebaine; D009020:Morphine; D003061:Codeine