Synthesis of 3-Benzyloxy-6-methyl-7-methoxyphenanthrene-9-carboxaldehyde with Utilize Intramolecular Heck Reaction as the Key Step  

作　　者：SONG Yan-ling ZHAI Xin SUN Zhi-feng KIM Sang-hee GONG Ping 

机构地区：[1]School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China [2]School of Chemical Engineering, Shenyang Institute of Chemical Technology, Shenyang 110042, P. R. China [3]College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea

出　　处：《Chemical Research in Chinese Universities》2008年第4期445-448,共4页高等学校化学研究（英文版）

摘　　要：The substituted phenanthrene-9-carboxyaldehydes are very important intermediates for the syntheses of phenanthroindolizidine and phenanthroquinolizidine alkaloids. The novel title compound was prepared from the reaction of 5 steps starting from the condensation of 3-methoxyl-4-methyl-phenylacetic acid and 4-（benzyloxy）-2-iodobenzaldehyde, followed by esterification, cyclization, reduction, and oxidation. A new method for the preparation of phenanthrene ring via palladium-catalyzed intramolecular Heck reaction was described. The title compound was characterized by IR, ^1H NMR, ^13C NMR, elemental analysis, and MS.The substituted phenanthrene-9-carboxyaldehydes are very important intermediates for the syntheses of phenanthroindolizidine and phenanthroquinolizidine alkaloids. The novel title compound was prepared from the reaction of 5 steps starting from the condensation of 3-methoxyl-4-methyl-phenylacetic acid and 4-（benzyloxy）-2-iodobenzaldehyde, followed by esterification, cyclization, reduction, and oxidation. A new method for the preparation of phenanthrene ring via palladium-catalyzed intramolecular Heck reaction was described. The title compound was characterized by IR, ^1H NMR, ^13C NMR, elemental analysis, and MS.

关 键 词：Phenanthrene-9-carboxyaldehyde Synthesis Heck reaction 

分 类 号：O623.5[理学—有机化学]