Short, asymmetric synthesis of epi-morphine ACNO analogues

Nicolas Heureux, Johan Wouters, Bernadette Norberg, István E. Markó

Research output: Contribution to journalArticle

Abstract

The short synthesis of ACNO analogues of morphine and the development of an asymmetric version of this polycyclization methodology was investigated. It was found that the oxygenated five-membered ring of the compound could be derived from the imine which may originate from tetracycle by oxidation of the aniline nitrogen and chemoselective removal of the ketone function. An enantioselective version of this methodology was also delineated for the rapid assembly of the ACNO analogues. The completion of the asymmetric synthesis of intermediate compound required the removal of the carboxymethyl auxiliary. The results show that tetracycle compound could be isolated in a overall yield of 67% from applying this methodology to the synthesis of naturally occurring opioids.

Original languageEnglish
Pages (from-to)3898-3900
Number of pages3
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number21
DOIs
Publication statusPublished - 25 Oct 2006

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  • Datasets

    CCDC 608856: Experimental Crystal Structure Determination

    Heureux, N. (Contributor), Marko, I. E. (Contributor), NORBERG, B. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007

    Dataset

    CCDC 608857: Experimental Crystal Structure Determination

    Heureux, N. (Contributor), Marko, I. E. (Contributor), NORBERG, B. (Contributor) & WOUTERS, J. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2007

    Dataset

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