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Communication | Regular issue | Vol 51, No. 2, 1999, pp.249-253
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8400
Unprecedented Cyanation and Cyanomethylation Following Ring Closure versus Dimer Formation during Anodic Oxidation of the Aspidofractinine Alkaloid Kopsamine

Toh-Seok Kam,* Tuck-Meng Lim, and Guan-Huat Tan

*Department of Chemistry, Unviersity of Malaya, Pantai Valley, 50603 Kuala Lumpur, Malaysia

Abstract

Anodic oxidation of the aspidofractinine-type indole alkaloid kopsamine on platinum in Et4NClO4/MeCN results in an unprecedented cyanation-cynomethylation reaction following ring closure while oxidation on vitreous carbon in LiClO4-MeOH yielded a dimerization product with a C2 element of symmetry.