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Paper | Special issue | Vol 97, No. 1, 2018, pp.422-430
Published online, 26th February, 2018
DOI: 10.3987/COM-18-S(T)30
A Short Synthesis of 9-Fluoroellipticine from 5-Fluoroindole

Deborah A. Davis and Gordon W. Gribble*

*6128 Burke Laboratory, Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, U.S.A.

Abstract

A synthesis of 9-fluoroellipticine (1c) from 5-fluoroindole (6) is described that features the regioselective lithiation of 5-fluoro-1-(phenylsulfonyl)indole (7) followed by chemoselective acylation of 3,4-pyridinedicarboxylic anhydride. Subsequent cyclization of keto acid 9 to keto lactam 10 with acetic anhydride and sequential treatment of 10 with methyllithium and sodium borohydride affords 9-fluoroellipticine.