Abstract

The structure of dihydronitraraine (I) has been established on the basis of the results of a study of its chemical properties and spectral characteristics and also of a correlation with nitraraine. An internal quaternary salt of (I) has been obtained and, by means of a directed change in the configuration at C3 in (I), the complete stereochemistry of the nitraraine and dihydronitraraine molecules have been determined: (±)-16-hydroxymethyl-3α,15α,20α-yohimb-16-ene and (±)-16β-hydroxymethyl-3α,15α,20α-yohimbane, respectively.

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