Synlett 2002(6): 1005-1007
DOI: 10.1055/s-2002-31931
LETTER
© Georg Thieme Verlag Stuttgart · New York

A New Entry to Asymmetric Synthesis of 1-Substituted 1,2,3,4-Tetrahydro-β-carbolines Employing a Pyroglutamic Acid Derivative as a Chiral Auxiliary

Takashi Itoh, Kazuhiro Nagata, Masashi Yokoya, Michiko Miyazaki, Sachiko Ikeda, Yuji Matsuya, Yasuko Enomoto, Akio Ohsawa*
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan
Fax: +81(3)37845982; e-Mail: ohsawa@pharm.showa-u.ac.jp;
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Publication History

Received 4 April 2002
Publication Date:
07 February 2007 (online)

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Abstract

β-Carboline which was protected at N-9 by an acyl group derived from l-pyroglutamic acid reacted with allyltributyltin or silyl enol ethers in the presence of an alkyl chloroformate in a highly diastereoselective manner to give 1-substituted 1,2-dihydro-β-carbolines. The compounds were readily transformed to the corresponding asymmetric 1-substituted tetrahydro-β-carbolines that are common partial structures in a variety of indole alkaloids.