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Synthesis of the Racemic Form of (Z)‐1, 17‐Diaminooctadec‐9‐Ene, An Aliphatic Diamine From Coccinellidae, Determination of the Absolute Configuration of the (+)‐Naturally‐Occurring Antipode

par Braconnier, Marie-France ;Braekman, Jean Claude ;Daloze, Désiré
Référence Bulletin des Sociétés chimiques belges, 94, 8, page (605-613)
Publication Publié, 1985

Article révisé par les pairs

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Résumé :

The total synthesis of the title compound (1) has been achieved. Also reported is the use of lanthanide induced shifts in 1H NMR spectroscopy to assign the absolute configuration of the α‐carbon atom in chiral primary α‐methylalkylamines. Application of this empirical method to natural (+)‐1 shows that it has the R‐configuration at C‐17. Copyright © 1985 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim