Accession Number : AD0618813

Title :   THE STRUCTURE OF RETAMINE AND THE PARTIAL SYNTHESIS OF THE (--)-ENANTIOMORPH,

Corporate Author : NATIONAL RESEARCH COUNCIL OF CANADA OTTAWA (ONTARIO) DIV OF PURE CHEMISTRY

Personal Author(s) : Shin,Kju Hi ; Fonzes,L. ; Marion,Leo

Report Date : 03 MAR 1965

Pagination or Media Count : 7

Abstract : Previous work by many authors has led to the assumption that retamine might be (+)-12-hydroxysparteine. A partial synthesis of the enantiomorph of this compound was effected by dehydration of (+)-13-hydroxylupanine and hydroboration of the product. The dehydration product consisted of two components that were separated by thin-layer chromatography and identified by the characteristics of their nuclear magnetic resonance (n.m.r.) spectra as delta 12,13- and delta 13,14-dehydrolupanine. Hydroboration of the delta 12,13-isomer gave rise to (-)-12 hydroxysparteine having, in thinlayer chromatography, the same Rf value as natural retamine and the same optical rotation numerically, although of opposite sign. The synthetic base had the same infrared and n.m.r. spectra as the alkaloid and the two had superimposable Debye-Scherrer patterns. Evidence is given showing the hydroxyl to be equatorial. (Author)

Descriptors :   (*ALKALOIDS, MOLECULAR STRUCTURE), NITROGEN HETEROCYCLIC COMPOUNDS, MOLECULAR ISOMERISM, MOLECULAR ROTATION, SYNTHESIS(CHEMISTRY), CHROMATOGRAPHIC ANALYSIS, NUCLEAR MAGNETIC RESONANCE, INFRARED SPECTRA, X RAY DIFFRACTION, CANADA

Distribution Statement : APPROVED FOR PUBLIC RELEASE