Chinese Journal of Organic Chemistry >
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).
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.
Shi Shengbin , Fan Guijuan , Yang Shiyuan , Li Jinshan , Liao Longyu . A Novel Synthetic Method of Endo-pentacyclo[5.4.0.02,6.03,10.05,9]- undecane-8-ol[J]. Chinese Journal of Organic Chemistry, 2014 , 34(5) : 1010 -1014 . DOI: 10.6023/cjoc201311009
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