Stereocontrolled synthesis of naturally occurring cladiellin oxacycles

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Project objective

Research objectives and content The cladiellin and eunicellin oxacycles, together with eleutherobin, constitute a family of potential antitumour medium ring ether natural products. The research programme involves the following objectives: (i) Petasis methylenation of vinyl-substituted cyclic carbonates, followed by (3.3) sigmatropic rearrangement, to give medium ring lactones. (ii) Elaboration of 9-membered lactones to 2,9-divinyl substituted oxonins for ring closing methathesis to eleutherobin analogues. (iii) Synthesis of a naturally occurring cladiellane by intramolecular Diels-Alder cycloaddition of a 2,9-disubstituted oxonin. (iv) Evaluation of the synthetic materials as potential cytotoxic agents. This work programme will last 24 months. Training content (objective, benefit and expected impact) The objective of the programme is to acquire experience in multistep natural product synthesis in a stimulating research active environment. In addition to the development of new synthetic methodology and generation of cytotoxic compounds, the experience gained is expected to enable the applicant to continue with an independent academic career. Links with industry / industrial relevance (22) Glaxo-Wellcome and Smithkline Bechham pharmaceuticals have an active interest in the research programme and will evaluate materials.

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Participants

• University of Cambridge · CambridgeCoordinatorUnited Kingdom

Links

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