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Paper | Special issue | Vol 82, No. 1, 2010, pp.349-370
Published online, 19th March, 2010
DOI: 10.3987/COM-10-S(E)5
Synthesis of 1,2,3,4,5,7-Hexahydro-6H-azocino[4,3-b]indol-6-ones as Intermediates for the Synthesis of Apparicine

Jason G. Kettle, David Roberts, and John A. Joule*

*The School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, U.K.


1-Phenylsulfonylindole is converted in eight steps into 2-(2-iodo-(Z)-but-2-en-1-yl)-6-methyl-1,2,3,4-tetrahydroazocino[4,3-b]indole, previously converted in one step into the indole alkaloid apparicine. The syntheses of other hexahydroazocino[4,3-b]indole potential precursors to the alkaloid are also described.