- Stereoselective Synthesis of a cis-Cedrane-8,9-diol as a Key Intermediate for an Amber Odorant
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The naturally occurring (-)-α-cedrene exhibits a weak woody and cedarlike odor. In contrast, cis-cedrene acetonide, which is a derivative of cedrene, is an extremely powerful semisynthetic aroma molecule. The current process starting from cedrene yields cis-cedrene acetonide in an overall yield of 99% yield.
- Stefanow, Vivian,Grandane, Aiga,Eh, Marcus,Panten, Johannes,Spannenberg, Anke,Werner, Thomas
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supporting information
p. 89 - 97
(2021/01/09)
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- Novel and versatile photosensitized oxygenation reaction of α-cedrene
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Three types of photosensitized oxygenations of α-cedrene (CED) were investigated, including: rose bengal(RB)-sensitized photooxygenation of α-cedrene in acetonitrile produced one major stereospecific product (cedr-8-exoen-9α-ol), in which the double bond migrated to an adjacent position, this result demonstrated the singlet oxygen process; 9,10-dicyanoanthrathene (DCA) sensitized photooxygenation led to the formation of cedr-8-en-10β-ol; benzyl (BZ)-sensitized photoepoxidation furnished a stereospecific 8α,9α-cedrene epoxide, this reaction includes radical reaction mechanism.
- Wu, Weiping,An, Feng,Geng, Zhengsong,Zhang, Ronghua,Jiang, Zhiqin
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p. 223 - 227
(2013/07/26)
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