Abstract
The chiral synthesis of the immunosuppressive sesquiterpene, FR65814 1 is described. The cyclohexane ring in 1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the carbon side-chain in 1 was stereoselectively introduced via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative, followed by Pd-catalyzed Stille coupling. The bis-epoxide function was stereoselectively constructed by sulfur ylide chemistry and vanadium catalyzed epoxidation of a homoallyl alcohol derivative. This first total synthesis fully confirmed the proposed absolute structure of FR65814.
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