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Synthesis 2014; 46(11): 1506-1510
DOI: 10.1055/s-0033-1340988
DOI: 10.1055/s-0033-1340988
paper
An Efficient Synthesis of Katsube Nitrile: A Key Building Block for Eburnamine-Vincamine Alkaloids
Further Information
Publication History
Received: 13 January 2014
Accepted after revision: 21 February 2014
Publication Date:
26 March 2014 (online)
Abstract
A novel synthesis of the Katsube nitrile is achieved via an efficient diastereoselective Pictet–Spengler cyclization of 3-ethyl-2-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-6-oxopiperidine-3-carbonitrile to construct the cis-[CD] rings in 1-ethyl-4-oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-carbonitrile, and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) catalyzed condensation of tert-butyl 4-cyano-4-(hydroxymethyl)hexanoate with tryptamine to assemble 4-cyano-4-(hydroxymethyl)-N-[2-(1H-indol-3-yl)ethyl]hexanamide as the key steps.
Key words
eburnamine-vincamine alkaloids - Katsube nitrile - Pictet–Spengler cyclization - cis-diastereoselectivity - 1,5,7-triazabicyclo[4.4.0]dec-5-eneSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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