Total Synthesis of the Litophynins, Ether-Bridged Cembranoid Natural Products of Marine Origin

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The proposed research programme concerns the total synthesis of members of the litophynin family of marine natural products. The litophynins are a sub-class of the cladiellin family of bridged cembranoids that possess significant biological activities and have not been synthesised previously. The research programme will focus on the discovery of novel routes to the litophynins that will be sufficiently efficient and general to be adapted to the construction of many of the numerous structurally related bioactive marine natural products.The intended synthetic approach to the rapid construction of the highly functionalised bridged-ether core of the litophynins will incorporate metal carbenoid and rearrangement methodology pioneered by the Clark Group. A variety of efficient annulation strategies will then be employed to build the tricyclic structure of the litophynins, and subsequent elaboration will be used to prepare individual members of the family.