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Paper | Special issue | Vol 79, No. 1, 2009, pp.955-965
Published online, 11th December, 2008
DOI: 10.3987/COM-08-S(D)71
A New Synthetic Route to the 1-Oxygenated Carbazole Alkaloids, Mukonine and Clausine E (Clauzoline I)

Shigeo Tohyama, Tominari Choshi, Shuhei Azuma, Haruto Fujioka, and Satoshi Hibino*

*Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan

Abstract

A new synthesis of the 1-oxygenated 1,3-disubstituted carbazole alkaloids, mukonine (1a) and clausine (1f) is described. The construction of the carbazole framework is based on an allene-mediated electrocyclic reaction involving the indole 2,3-bond. The 1,3-disubstituted 1-oxygenated carbazoles 1a and 1f are derived from the 1,2,3-trisubstituted carbazole.