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A concise route to iboga-analogues via the formation of suitably substituted-2-indoles

✍ Scribed by Goutam Kumar Jana; Surajit Sinha

Publisher: Elsevier Science
Year: 2010
Tongue: French
Weight: 359 KB
Volume: 51
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2010.02.028

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✦ Synopsis

A concise route to iboga-analogues has been developed. Important steps include a Pd-catalyzed Sonogashira coupling of Boc-2-idodaniline with terminal alkynes and the formation of 2-substituted indoles in the presence of tetrabutylammonium fluoride to give the key intermediate, dehydroisoquinuclidinecontaining indole. The final step cyclization between indole-3-position and dehydroisoquinuclidine ring was achieved using Pd(II)-Ag(I) mixed metal-mediated cyclization method. Both exo-and endo-substitution with -CO 2 Me at C19 have been reported.

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