Synthesis 2014; 46(11): 1506-1510
DOI: 10.1055/s-0033-1340988
paper
© Georg Thieme Verlag Stuttgart · New York

An Efficient Synthesis of Katsube Nitrile: A Key Building Block for Eburnamine-Vincamine Alkaloids

Xiaofei Chen
a   Department of Chemistry, Fudan University, Shanghai 200433, P. R. of China
b   Institutes of Biomedical Science, Fudan University, Shanghai 200433, P. R. of China   Fax: +86(21)65643811   eMail: rfchen@fudan.edu.cn
,
Fener Chen*
a   Department of Chemistry, Fudan University, Shanghai 200433, P. R. of China
b   Institutes of Biomedical Science, Fudan University, Shanghai 200433, P. R. of China   Fax: +86(21)65643811   eMail: rfchen@fudan.edu.cn
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Publikationsverlauf

Received: 13. Januar 2014

Accepted after revision: 21. Februar 2014

Publikationsdatum:
26. März 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.

Supporting Information

 
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