Add time:08/08/2019         Source:sciencedirect.com

The alcohols cis-5-hydroxy-cyclogeraniol and cis-α-epoxy-cyclogeraniol can be easily prepared with high diastereoisomeric purity starting from ethyl-α-cyclogeraniate. A few straightforward chemical transformations allow their conversion into tetrahydroactinidiolide and dihydroactinidiolide, two relevant natural flavors of carotenoid origin. The two starting C10 alcohols can also be obtained in enantioenriched form by means of an optimized lipase-mediated resolution procedure. The fractional crystallization of the obtained enantioenriched tetrahydroactinidiolide proved to be very efficient, allowing the preparation of both tetrahydroactinidiolide and dihydroactinidiolide in enantiopure form (ee >98%). Finally, a comprehensive study on the oxidation of tetrahydroactinidiolide to dihydroactinidiolide was accomplished by devising a new selenium-free chemical process for this type of transformation.

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