The Synthesis of Isoquinoline Alkaloid and Its Related Compounds Using Alanine Derivatives as Chiral Auxiliaries

Takashi Itoh; Kazuhiro Nagata; Masashi Yokoya; Michiko Miyazaki; Keiko Kameoka; Shigeru Nakamura; Akio Ohsawa

doi:10.1248/cpb.51.951

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The Synthesis of Isoquinoline Alkaloid and Its Related Compounds Using Alanine Derivatives as Chiral Auxiliaries

Takashi Itoh, Kazuhiro Nagata, Masashi Yokoya, Michiko Miyazaki, Keiko Kameoka, Shigeru Nakamura, Akio Ohsawa

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Keywords: asymmetric synthesis, indole alkaloid, chiral auxiliary, pentamethoxyhomoprotoberberine, O-methylkreysigine, hexahydropyrrolo[2,1-a]isoquinoline

JOURNAL FREE ACCESS

2003 Volume 51 Issue 8 Pages 951-955

DOI https://doi.org/10.1248/cpb.51.951

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Abstract

Chiral 1-substituted isoquinoline derivatives, which were obtained by the reaction using alanine derivatives as chiral auxiliaries, were transformed to (S)-2,3,9,10,11-pentamethoxyhomoprotoberberine (7) and a synthetic intermediate for O-methylkreysigine (9) in good yields and high stereoselectivity. The corresponding chiral allyl derivative of isoquinoline was transformed to a pyrrolidinoisoquinoline (16) in a highly enantioselective manner.

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