Oxidative Transformations of Indole Alkaloids. II. The Preparation of Oxindoles from cis-DE-Yohimbinoid Alkaloids. The Partial Synthesis of Carapanaubine

Journal of the American Chemical Society
1963.0

Abstract

The reaction of lead tetracarboxylates with yohimbine, methyl reserpate and related alkaloids affords acyloxyindolenines. These compounds on reflux in methanolic acetic acid yield the corresponding oxindoles. Use of this observation has been made to transform reserpiline into carapanaubine, thereby defining the complete stereochemistry of this new alkaloid. The mechanism by which the acyloxyindolenines are formed and the mechanism of the rearrangement step are discussed. © 1963, American Chemical Society. All rights reserved.

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