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Efficent synthesis of hemibrevetoxin B by deployment of new strategies for polyether construction (SYNTOFHB)
Start date: 02 Oct 2007, End date: 01 Oct 2009 PROJECT  FINISHED 

The proposed programme of research concerns the implementation of linear and two-directional strategies for the rapid total synthesis of the marine polyether natural product hemibrevetoxin B using novel ring-closing metathesis (RCM) methodology. Both of these approaches will employ catalytic RCM reactions of enol ethers, allylic ethers and alkynyl ethers that have been developed in the Clark Research Group in order to construct the cyclic ethers that are embedded in the fused tetracyclic structure of hemibrevetoxin B. A total synthesis of hemibrevetoxin B with a longest linear sequence of less than 30 steps from readily available starting materials should be achievable using the strategies outlined in the proposal. Hemibrevetoxin B is the smallest of the laddered polyether natural products but the strategies developed for the synthesis of this compound should be directly applicable to the synthesis of the larger bioactive members of this family of natural products such as the ciguatioxins and gambieric acids.
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