Synthesis of yohimbines. 4. Synthesis of (±)-3-epi-α-yohimbine and (±)-3,17-epi-α-yohimbine. Carbon-13 nuclear magnetic resonance investigation of yohimbine stereoisomers

Katalin Honty, Eszter Baitz-Gács, Gábor Blaskó, Csaba Szántay

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26 Citations (Scopus)

Abstract

By use of the method developed earlier for epimerization at C(3) and C(16) the first synthesis of (±)-3-epi-α-yohimbine (1) and (±)-3,17-epi-α-yohimbine (3) was accomplished. Comparative analysis of the carbon-13 chemical shift data for isomeric yohimbines with natural and nonnatural stereochemistry has provided the predominant conformations in the normal, allo, and epi-allo series.

Original languageEnglish
Pages (from-to)5111-5114
Number of pages4
JournalJournal of Organic Chemistry
Volume47
Issue number26
Publication statusPublished - 1982

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Stereoisomerism
Yohimbine
Carbon
Nuclear magnetic resonance
Stereochemistry
Chemical shift
Conformations

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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T1 - Synthesis of yohimbines. 4. Synthesis of (±)-3-epi-α-yohimbine and (±)-3,17-epi-α-yohimbine. Carbon-13 nuclear magnetic resonance investigation of yohimbine stereoisomers

AU - Honty, Katalin

AU - Baitz-Gács, Eszter

AU - Blaskó, Gábor

AU - Szántay, Csaba

PY - 1982

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AB - By use of the method developed earlier for epimerization at C(3) and C(16) the first synthesis of (±)-3-epi-α-yohimbine (1) and (±)-3,17-epi-α-yohimbine (3) was accomplished. Comparative analysis of the carbon-13 chemical shift data for isomeric yohimbines with natural and nonnatural stereochemistry has provided the predominant conformations in the normal, allo, and epi-allo series.

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