五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇的合成新方法
收稿日期: 2013-11-07
修回日期: 2013-12-24
网络出版日期: 2014-01-16
基金资助
国家重大基础研究（No. 00401010201）资助项目.
A Novel Synthetic Method of Endo-pentacyclo[5.4.0.02,6.03,10.05,9]- undecane-8-ol
Received date: 2013-11-07
Revised date: 2013-12-24
Online published: 2014-01-16
Supported by
Project supported by the National Key Basic Research Grant Foundation (No. 00401010201).
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.
史胜斌 , 范桂娟 , 杨世源 , 李金山 , 廖龙渝 . 五环[5.4.0.02,6.03,10.05,9]十一烷-内-8-醇的合成新方法[J]. 有机化学, 2014 , 34(5) : 1010 -1014 . DOI: 10.6023/cjoc201311009
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.
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