摘要
从柠檬醛出发，经环化、氰基化、烯丙位氧化、水解及环化还原等５步反应，合成了（±）－耳壳藻内酯（１）。
The total synthesis of(±)caulilide(1) which shows a potent cytotoxicity is described. Cyclocitral(2) was prepared from citral via citralylimine in 85%～90% yield. The reaction of 2 with KCN followed by dehydration afforded nitrile 3 in 56% yield. Allyl oxidation of 3 was performed by using pyridium dichromate-t-butyl-hydroperoxide to give ketonitrile(4) which was a mixture of geometrie isomers of 4a(cis) and 4b(trans). After separation on a silica gel column, the cis isomer 4a was then hydrolyzed and simultaneously lactonized in conc. HCl solution to form a lactone(±)-5. The synthesis of caulilide(1) was completed by the reduction of 5 with NaBH4. The crude product was separated by high performed chromatography to give the target compound (±)-1.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
1996年第5期743-746,共4页
Chemical Journal of Chinese Universities
基金
国家自然科学基金
国家教育委员会博士学科点基金
关键词
耳壳藻内酯
全合成
高单萜内酯
柠檬醛
Caulilide, Total synthesis, Homo-monoterpene lactone, Citral
