Partial Synthesis of Rauwolfia Alkaloids, Vomilenine and (19Z)-Vomilenine, and Their Relative Thermodynamic Stability as Revealed by Their Transformation into Perakine

Hiromitsu TAKAYAMA; Chada PHISALAPHONG; Mariko KITAJIMA; Norio AIMI; Shin-ichiro SAKAI; Joachim STOCKIGT

doi:10.1248/cpb.39.266

Hiromitsu TAKAYAMA, Chada PHISALAPHONG, Mariko KITAJIMA, Norio AIMI, Shin-ichiro SAKAI, Joachim STOCKIGT

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Keywords: Rauwolfia alkaloid, indole alkaloid, ajmaline, vomilenine, (19Z)-vomilenine, perakine, partial synthesis, structure elucidation, differential NOE experiment, thermodynamic stability

JOURNAL FREE ACCESS

1991 Volume 39 Issue 2 Pages 266-269

DOI https://doi.org/10.1248/cpb.39.266

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Abstract

The geometry of the ethylidene side chain in vomilenine (1) was proven to be (19E) by the spectroscopic analysis of the synthetic intermediates from ajmaline (2) to vomilenine (1). The relative thermodynamic stability of vomilenine (1) and (19Z)-vomilenine (19), as revealed by their transformation into perakine (9), is discussed.

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