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Synthesis 2012(3): 409-416  
DOI: 10.1055/s-0031-1289656
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Approaches to Highly Functional β-Carboline Building Blocks via Allylic Amidation

Johannes F. Teichert, Martín Fañanás-Mastral, Ben L. Feringa*
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands
Fax: +31(50)3634296; e-Mail: b.l.feringa@rug.nl;
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Publication History

Received 7 November 2011
Publication Date:
22 December 2011 (online)

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Abstract

A new, straightforward synthesis of highly functional β-carboline building blocks is presented that makes use of allylic amidation methodology. The products obtained carry a terminal double bond as well as an easy-to-deprotect amide, which make them perfectly suitable for further functionalization. The use of the trifluoroacetamide group is exploited in a dual fashion; it acts as a protecting group and functions as the nucleophile for the allylic amidation reaction.

Key words

indoles - β-carbolines - allylic amidation - heterocycles - Stille reaction

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N-Benzyltryptamine 7b could also be trapped with acrolein after lithiation to give secondary allylic alcohol 12 (Scheme 6). See the experimental section for details.

Scheme 6