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Title: Facile and efficient synthesis of isolongifolenone

Author
item WANG, SHIFA - VPI- VA. TECH
item Zhang, Aijun

Submitted to: Organic Preparation Proceeds International
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 7/2/2008
Publication Date: 8/1/2008
Citation: Wang, S., Zhang, A. 2008. Facile and efficient synthesis of isolongifolenone. Organic Preparation Proceeds International. 40(4):405-410.

Interpretive Summary: A chemical isolated from leaves and stems of a certain tree has been used as fragrance in many commercial products. This same compound has also often been added in cosmetics for skin whitening and pigment removing after sunburn. Recently, we discovered that this compound could repel two kinds of mosquitoes and two kinds of ticks. One of the limitations is the ability to provide this compound in sufficient quantity and purity for further investigations. We have developed a facile and efficient method for producing this compound in short time with high purity and yield, which will lead to the wider availability of this chemical for various industrial and clinical usages, e.g. for testing as a natural repellent to protect humans against diseases vectored by blood-feeding mosquitoes and ticks. Especially, it has high potential for military usage to protect soldiers from mosquito and/or sand fly bites.

Technical Abstract: An efficient method for preparation of isolongifolenone by oxidation of isolongifolene in high yield with a short reaction time is described. Highly allylic oxidation selectivity was achieved by using tert-butyl hydroperoxide as the oxidant and chromium hexacarbonyl as the catalyst. The oxidative selectivity and capacity of different peroxide reagents to isolongifolene were also investigated and reported.