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Synfacts 2006(9): 0889-0889  
DOI: 10.1055/s-2006-949206
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Modular Synthesis of Fused Indole Derivatives

Contributor(s): Victor Snieckus, Heiko Scharl
A. B. Smith, III*, L. Kürti, A. H. Davulcu
University of Pennsylvania, Philadelphia, USA
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Complementary routes to strained doubly cycloalkyl-fused indole derivatives using modern cross-coupling methodology are reported. Stille coupling of 7-stannylated indoline with 2-iodo cyclic enones leads to the key intermediate A which, by reduction and LiHMDS-mediated triflation using Comins’ excellent reagent, gives isomeric triflates. The latter compounds are deprotected and transformed to the tetracyclic indole derivative B by the Buchwald-Hartwig C-N coupling tactic or, directly, by acid-catalyzed cyclization. The overall yields are reasonable but the scope in terms of benzene-moiety substitution and variable cycloalkyl ring size remains to be explored.