五环[5.4.0.0^(2,6).0^(3,10).0^(5,9)]十一烷-内-8-醇的合成新方法

A Novel Synthetic Method of Endo-pentacyclo[5.4.0.0^(2,6).0^(3,10).0^(5,9)]-undecane-8-ol

五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇是合成抗流感病毒医药、抗发炎药物、高能量燃料和燃料添加剂的关键中间体,本研究以环戊二烯和对苯醌为起始原料,经过Diels-Alder、光环化、羰基保护、氢化铝锂还原、水解、黄鸣龙还原等6步反应合成五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇,总产率达44.9%.本方法操作简便,分离纯化容易,成本低廉,收率高,为五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇的规模化合成奠定了基础.

Endo-pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8-ol（5） was a key intermediate in the research of anti-influenza viruses medicines, anti-inflammatory drugs, high energy fuels and fuel additives. The synthesis of endo-pentacyclo-[5.4.0.02,6.03,10.05,9]undecane-8-ol（5） was successfully achieved by a six steps route which was consisted of Diels-Alder, photo-cyclo addition, carbonyl protecting, lithium aluminium hydride reduction, hydrolysis and Huang-Minlon reduction. The total yield was 44.9%. This method has the advantages of facilely available starting materials, simply conducted procedures, relatively high yield and easy purification, and is more suitable for scale-up production.