Skip to main content

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

Buy Article:

$60.90 plus tax (Refund Policy)

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: https://doi.org/10.1080/00397910802238684

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

Publication date: 2008-01-01

  • Access Key
  • Free ContentFree content
  • Partial Free ContentPartial Free content
  • New ContentNew content
  • Open Access ContentOpen access content
  • Partial Open Access ContentPartial Open access content
  • Subscribed ContentSubscribed content
  • Partial Subscribed ContentPartial Subscribed content
  • Free Trial ContentFree trial content
Cookie Policy
X
Cookie Policy
Ingenta Connect website makes use of cookies so as to keep track of data that you have filled in. I am Happy with this Find out more