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Enzymatic resolution of (+/-)-gamma-cyclohomogeraniol and conversion of its (S)-isomer to (S)-gamma-coronal, the ambergris odorant.

Bioorganic & Medicinal Chemistry 7(5):723 (1999) PMID 10400325

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.