Facile Synthesis of 2,3,6,11-Tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-Carboxylic Acid Methyl Ester via a 9-BBN-Mediated Tertiary Lactam Reduction

Authors: Fokas, Demosthenes; Wang, Zhimin

Source: Synthetic Communications, Volume 38, Number 21, January 2008 , pp. 3816-3822(7)

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Abstract:

A facile synthesis of 2,3,6,11-tetrahydro-1H,5H-indolizino[8,7-b]indole-11b-carboxylic acid methyl ester, a versatile intermediate utilized in the synthesis of indole alkaloids, was achieved in two steps. Condensation of tryptamine with dimethyl α-ketoglutarate led to the formation of the corresponding indolizino[8,7-b]indolone ester, which subsequently underwent an efficient lactam reduction with 9-BBN to generate the tertiary amine ester in good yield.

Keywords: 9-BBN; Dimethyl α-ketoglutarate; lactam reduction; tryptamine

Document Type: Research article

DOI: http://dx.doi.org/10.1080/00397910802238684

Affiliations: 1: Department of Chemistry, ArQule, Inc., Woburn, Massachusetts, USA

Publication date: 2008-01-01