Formation of an Unusual Dimeric Compound by Lead Tetraacetate Oxidation of a Corynanthe-Type Indole Alkaloid, Mitragynine

Hiromitsu Takayama; Hayato Ishikawa; Mariko Kitajima; Norio Aimi

doi:10.1248/cpb.50.960

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Formation of an Unusual Dimeric Compound by Lead Tetraacetate Oxidation of a Corynanthe-Type Indole Alkaloid, Mitragynine

Hiromitsu Takayama, Hayato Ishikawa, Mariko Kitajima, Norio Aimi

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Keywords: indole alkaloid, oxidation, dimerization, lead tetraacetate, indolenine, reaction mechanism

JOURNAL FREE ACCESS

2002 Volume 50 Issue 7 Pages 960-963

DOI https://doi.org/10.1248/cpb.50.960

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Abstract

Lead tetraacetate oxidation of a Corynanthe-type indole alkaloid, mitragynine, produced mainly 7-acetoxyindolenine derivative (2) together with a dimeric compound (4) as a minor product. The novel structure having a bridge between the C-11′ and C-7 positions in the respective indolenine parts and its formation mechanism were studied.

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