Practical synthesis of (-)-morphine

Johann Mulzer, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish (US)
Pages (from-to)475-482
Number of pages8
JournalChirality
Volume11
Issue number5-6
DOIs
StatePublished - 1999

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Hydrocodone
Optical Rotation
Alkaloids
Morphine
Cellulose
Derivatives
cellulose triacetate

Keywords

  • Asymmetric synthesis of morphinane derivatives
  • Chiral resolution by column chromatography
  • Conjugate cuprate addition

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Practical synthesis of (-)-morphine. / Mulzer, Johann; Trauner, Dirk.

In: Chirality, Vol. 11, No. 5-6, 1999, p. 475-482.

Research output: Contribution to journalArticle

Mulzer, Johann ; Trauner, Dirk. / Practical synthesis of (-)-morphine. In: Chirality. 1999 ; Vol. 11, No. 5-6. pp. 475-482.
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