Synthesis of enantiomerically pure morphine alkaloids: The hydrophenanthrene route

Dirk Trauner, Jan W. Bats, Andreas Werner, Johann Mulzer

Research output: Contribution to journalArticle

Abstract

A concise, linear, total synthesis of (-)-dihydrocodeinone - a close synthetic precursor of (-)-codeine and (-)-morphine - has been achieved. The carbocyclic core of the alkaloid was provided in the form of a phenanthrenone, which was resolved by chromatography on cellulose triacetate. A cuprate conjugate addition was used to establish the crucial benzylic quaternary stereocenter and to introduce the C2-side chain. Dimeric byproducts provide evidence for a single electron transfer (SET) mechanism. Unusual S(N)2 and radical cyclizations were employed for the formation of the dihydrobenzofuran and the piperidine ring, respectively.

Original languageEnglish (US)
Pages (from-to)5908-5918
Number of pages11
JournalJournal of Organic Chemistry
Volume63
Issue number17
DOIs
StatePublished - Aug 21 1998

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Hydrocodone
Codeine
Cyclization
Chromatography
Alkaloids
Morphine
Byproducts
Electrons
cellulose triacetate
piperidine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of enantiomerically pure morphine alkaloids : The hydrophenanthrene route. / Trauner, Dirk; Bats, Jan W.; Werner, Andreas; Mulzer, Johann.

In: Journal of Organic Chemistry, Vol. 63, No. 17, 21.08.1998, p. 5908-5918.

Research output: Contribution to journalArticle

Trauner, Dirk ; Bats, Jan W. ; Werner, Andreas ; Mulzer, Johann. / Synthesis of enantiomerically pure morphine alkaloids : The hydrophenanthrene route. In: Journal of Organic Chemistry. 1998 ; Vol. 63, No. 17. pp. 5908-5918.
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