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

Journal of the American Chemical Society

Volumn 131, Issue 32, 2009, Pages 11402-11406

  Stork, Gilbert ^a   Yamashita, Ayako ^a   Adams, Julian ^a,b   Schulte, Gary R ^a,c   Chesworth, Richard ^a,d   Miyazaki, Yoji ^a,e   Farmer, Jay J ^a,f  

^a Columbia University ^*  (United States)

^b Infinity Pharmaceuticals Inc   (United States)

^c Kahuna Scientific Consulting LLC   (United States)

^d EnVivo Pharmaceuticals   (United States)

^e UNIVERSITY OF TOKYO   (Japan)

^f Novomer   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[4 + 2] CYCLOADDITION; REGIOSPECIFIC; STEREOSELECTIVE FORMATION; STEREOSELECTIVE SYNTHESIS; TOTAL SYNTHESIS;

CARBOXYLIC ACIDS; ESTERS; OLEFINS; ORGANIC ACIDS; STEREOCHEMISTRY;

STEREOSELECTIVITY;

6 DEOXYCODEINE; ALKADIENE; BENZOFURAN DERIVATIVE; CODEINE; MORPHINE; PIPERIDINE; THEBAINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

CODEINE; MOLECULAR STRUCTURE; MORPHINE; STEREOISOMERISM; THEBAINE;

EID: 68949112541     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9038505     Document Type: Article

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