摘要
以 α-环柠檬醛 (1 )为 A环合成子 ,以季盐 (2 )为 C环合成子 ,经缩合及分子内环化反应得到关键中间体 (5 ) .为引入乙基 ,进行了 Friedel-Crafts反应和脱氧反应等 ,共经 7步反应得到了 (± ) -1 2 -乙基 -1 3-甲氧基 -8,1 1 ,1 3-罗汉松三烯 -7-酮 [(± ) -nimbonone](9)及 (± ) -1 2 -乙基 -1 3-甲氧基 -8,1 1 ,1 3-罗汉松三烯 (1 0 ) .
By using α-cyclocitral(1) as the A ring synthon, and triphenyl phosphonium chloride(2) as the C ring synthon, the key intermediate 5 was obtained after the condensation and intracyclization reactions. In order to introduce the ethyl substituent, Fiedel-Crafts acetylation had been first employed to synthesize compound 6, and then the carbonyl group in compound 6 was protected with 1,2-ethanedithiol to afford compound 7. Compound 7 was oxidized to afford compound 8. Desulfurization of compounds 7 and 8 with Raney Ni gave the desired products (±)-nimbonone (9) and (±)-12-ethyl-13- methoxy-8,11,13- podocarpatriene (10) respectively.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
2003年第6期1019-1022,共4页
Chemical Journal of Chinese Universities
基金
国家自然科学基金 (批准号 :2 0 172 0 2 3)资助
