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Synthesis 2005(1): 28-32  
DOI: 10.1055/s-2004-834915
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Total Synthesis of 1-Methoxycanthin-6-one: An Efficient One-Pot Synthesis of the Canthin-6-one Skeleton from β-Carboline-1-carbaldehyde [1]

Hideharu Suzuki*, Makoto Adachi, Yuki Ebihara, Hiroshi Gyoutoku, Hinako Furuya, Yasuoki Murakami, Hiroaki Okuno
Faculty of Pharmaceutical Sciences, Toho University 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan
Fax: +81(47)4721595; e-Mail: suzuki@phar.toho-u.ac.jp;
Further Information

Publication History

Received 25 June 2004
Publication Date:
17 November 2004 (online)

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Abstract

A total synthesis of naturally occurring 1-methoxycan-thin-6-one is described. In this synthesis, we achieved one-pot conversion from β-carboline-1-carbaldehyde to the canthin-6-one skeleton by the sequential addition of lithium ketene acetal in LiHMDS solution followed by the addition of EtOH in the reaction mixture.

Key words

indoles - β-carboline - alkaloids - aldol reaction - cyclization

    References

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2

Current address: Faculty of Pharmaceutical Sciences, Chiba Institute of Science, 3 Shiomi-cho, Choshi, Chiba 288-0025, Japan.