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Practical synthesis of (−)-morphine

✍ Scribed by Johann Mulzer; Dirk Trauner

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 173 KB
Volume: 11
Category: Article
ISSN: 0899-0042
DOI: 10.1002/(sici)1520-636x(1999)11:5/6<475::aid-chir20>3.0.co;2-g

No coin nor oath required. For personal study only.

✦ Synopsis

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.

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