Enzymatic resolution of (+/-)-gamma-cyclohomogeraniol and conversion of its (S)-isomer to (S)-gamma-coronal, the ambergris odorant.
Enzymatic acetylation of (+/-)-gamma-cyclohomogeraniol[2-(2',2'-dimethyl-6'-methylenecyc lohexyl)ethanol] with vinyl acetate in the presence of lipase AK yielded the acetate of its (R)-isomer, leaving its (S)-isomer intact. The (S)-isomer was chemically converted to (S)-gamma-coronal[2-methylene-4-(2',2'-dimethyl-6'-methylenecyclohexy l)butanal], the ambergris odorant.
Department of Chemistry, Faculty of Science, Science University of Tokyo, Japan.
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Horiuchi
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Takikawa
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Mori
D000080462:Acyclic Monoterpenes; D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry*; D018648:Ambergris / Q000737:chemistry*; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry*; D000431:Ethanol / Q000138:chemical synthesis* / Q000737:chemistry* / Q000031:analogs & derivatives; D007536:Isomerism; D008956:Models, Chemical; D013729:Terpenes / Q000737:chemistry* / Q000378:metabolism*
C121486:2-(2',2'-dimethyl-6'-methylenecyclohexyl)ethanol; C121487:2-methylene-4-(2',2'-dimethyl-6'-methylenecyclohexyl)ethanol; D000080462:Acyclic Monoterpenes; D000473:Alkanes; D018648:Ambergris; D003510:Cyclohexanes; D013729:Terpenes; D000431:Ethanol; C007836:geraniol