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Communication | Regular issue | Vol 14, No. 5, 1980, pp.585-587
Published online, 1st January, 1970
DOI: 10.3987/R-1980-05-0585
The Synthesis of Rugosinone and Ledecorine

Natesan Murugesan and Maurice Shamma*

*Department of Chemistry, The Pennsylvania State University, York Campus, P1031 Edgecomb Avenue, York, Pennsylvania 17403, U.S.A.

Abstract

Hydrolysis with concomitant air oxidation of polyberbine (5), derived from berberine chloride (6), furnished dihydrorugosinone (7) which underwent further air oxidation in ethanolic sodium hydroxide to give rugosinone (2). m-Chloroperbenzoic acid oxidation of coptisine chloride (8) afforded enamide 9 whose successive reduction using lithium aluminum hydride in THF and sodium borohydride in methanol supplied a mixture of norledecorine (10) and ledecorine (3). N-Methylation of 10 with formaldehyde and sodium borohydride gave rise to ledecorine (3) in high yield. Polycarpine (1), rugosinone (2), and ledecorine (3) probably arise in nature from protoberberines.