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

ASJC Scopus subject areas

  • Organic Chemistry

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