Gardneria Alkaloids(第8報)Gardneria Alkaloid類の相互変換, ならびに側鎖二重結合の配置について

概要

論文の詳細を見る
Hydroxygardnutine (IV) was converted to gardnution (II), whose absolute configuration is known, by the route shown in Chart 2,and the configuration of Δ^<19> of IV has been clarified from this fact. The aldehyde (VII), derived from IV, gave abnormal reduction products (VIII and IX) by the Huang-Minlon method. The reaction is explainable by the mechanism (shown on Chart 4.) A similar treatment of compound XIII, formed from gardneramine (I), resulted in the formation of (19Z)-18-demethoxygardneramine (XIX)(as shown in Chart 7.) Difference in the chemical shifts of C_<15>-H of natural (19E)-18-demethoxygardneramine (V) and XIX in their nuclear magnetic resonance spectra supports the above conclusion about the configuration of Δ^<19>. NOE effect was observed between C_<18>-CH_3 and C_<15>-H in compound (V) while there was no effect in XIX.
社団法人日本薬学会の論文
1974-02-25