A short route to enantiomerically pure benzophenanthridinone skeleton: synthesis of lactone analogues of narciclasine and lycoricidine

The Journal of Organic Chemistry
Said Ibn-AhmedYves Chapleur

Abstract

Condensation of functionalized o-toluamide anions on a carbohydrate-derived lactone, followed by intramolecular aldol cyclization, provides enantiomerically pure 2-arylcyclohexenones. Different approaches for the stereoselective transformation of the carbonyl group of these key intermediates into an amino group were unsuccessful. However 1,4-addition of thiolate and concomitant ring closure to isocoumarine provided a useful method for the transformation of the tertiary amide function. Opening of the isocoumarin with ammonia provided the corresponding amide and recovery of the enone system. Subsequent reductive amination of this cyclohexenone was found to depend on the nature of the protecting groups and led to the protected form of 4-epi- and -iso-narciclasine. Oxo analogues of narciclasine and epi-narciclasine and lycoricidine were also obtained after reduction of the enone and subsequent lactonization. They showed no biological activity as antitumor agents.

References

Nov 1, 1986·Journal of Natural Products·G R PettitY Sagawa
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Oct 17, 2003·Angewandte Chemie·Anh Nga PhungWolf-Dieter Fessner

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Citations

May 21, 2008·Chemical Reviews·Alexander Kornienko, Antonio Evidente
Mar 7, 2007·The Journal of Organic Chemistry·Albert Padwa, Hongjun Zhang
Sep 12, 2009·The Journal of Organic Chemistry·Madhuri ManpadiAlexander Kornienko
Jul 27, 2007·Natural Product Reports·Zhong Jin
Jul 9, 2008·Translational Oncology·Laurent IngrassiaRobert Kiss
Jul 16, 2011·Bioorganic & Medicinal Chemistry Letters·Sergey VshyvenkoAlexander Kornienko
Dec 5, 2012·Organic & Biomolecular Chemistry·Olaia Nieto-García, Ricardo Alonso
Mar 13, 2016·Angewandte Chemie·Mukund GhavreTomas Hudlicky
Jan 1, 2008·Organic Preparations and Procedures International·Madhuri Manpadi, Alexander Kornienko
Jan 1, 2012·Canadian Journal of Chemistry·Sergey VshyvenkoSiyaram Pandey
Aug 13, 2005·The Journal of Organic Chemistry·Ayodele O OlabisiKandatege Wimalasena

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