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Practical synthesis of (−)‐morphine
Author(s) -
Mulzer Johann,
Trauner Dirk
Publication year - 1999
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1999)11:5/6<475::aid-chir20>3.0.co;2-g
Subject(s) - chemistry , chirality (physics) , conjugate , derivative (finance) , stereochemistry , cellulose triacetate , combinatorial chemistry , organic chemistry , cellulose , chiral anomaly , mathematical analysis , physics , mathematics , fermion , quantum mechanics , financial economics , nambu–jona lasinio model , economics
The hydrophenanthrenone approach to the synthesis of morphinane alkaloids such as (−)‐dihydrocodeinone ( 16 ) is described. Optical activity is achieved by chiral resolution of the hydrophenanthrenone derivative 6 on cellulose triacetate. Key steps of the thirteen‐step synthesis are the conjugate addition of vinyl cuprate to 6 , which generates the crucial benzylic quaternary center and the demethylative cycloetherification step that transforms bromoketone 8 into morphinane 9 . Chirality 11: 475–482, 1999. © 1999 Wiley‐Liss, Inc.