Total synthesis of (±)-marmin (cas 14957-38-1) and related coumarin monoterpenes

Add time:07/18/2019    Source:sciencedirect.com

(±)-Marmin (1a) and its cis isomer (1b) have been synthesized from 7-neranyloxycoumarin (10a) and 7-neryloxycoumarin (10b), respectively, by way of the corresponding terminal epoxides 2a and 2a. The geometrically and positionally specific route confirms the structure and, in particular, the irons double bond geometry of natural (+)-marmin and epoxide (+)-2a. The latter, upon reaction with stannic chloride in benzene gives rise to the naturally occurring cyclic monoterpene coumarin types 3 and 6 as well as the previously unknown double-bond isomer 13.

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