β-フェンケンとシクロフェンケンの四酢酸鉛酸化

概要

論文の詳細を見る
β-Fenchene _??_1_??_ and cyclo-fenchene _??_2_??_ were oxidized with lead tetraacetate and hydrolyzed. The oxidation of _??_1_??_ gave exo-β-fenchol _??_3_??_, endo-5, 5-dimethyl-2-methylennorbornane-6-ol _??_4_??_, 5, 5-dimethyl-2-hydroxymethyl-2-norbornene _??_5_??_, R-homo-β-fenchenilone _??_6_??_ and endo-R-homo-β-fenchenilol _??_7_??_. In a similar oxidation procedure to _??_1_??_, seven products were obtained by _??_2_??_: iso-fenchone _??_8_??_, 2, 5, 5-trimethylnorbornane-6-one _??_9_??_, endo-iso-fenchol _??_10_??_, _??_4_??_, cy-clo-fenchenilalcohol _??_11_??_, exo-5, 5-dimethyl-2-methylennorbornane-6-ol _??_12_??_ and exo-7, 7-dimeth-yl-2-methylennorbornane-6-ol _??_13_??_. Their structure and stereochemistry were determined by MS, IR, 1H- and 13C-NMR spectra. Compounds _??_4_??_, _??_5_??_, _??_6_??_, _??_7_??_, _??_9_??_, _??_11_??_ and _??_12_??_ were novel monoterpene derivatives. Compounds _??_4_??_, _??_12_??_ and _??_13_??_ possessed a mild nojigiku-like odor.
社団法人日本農芸化学会の論文