The gambieric acids A�D (GAs, 1a�d , Fig. 1 ) are potent antifungal agents isolated by Yasumoto from a culture medium of the marine dinoflagellate Gambierdiscus toxicus. They have a unique polycyclic structure, consisting of nine contiguous trans-fused polyether rings (B�J) with an isolated tetrahydrofuran ring (A) and 27 stereogenic centers. Sasaki recently proposed a reassignment of the absolute configuration of the nonacyclic polyether core 2 , albeit total synthesis is required in order to confirm its stereochemical assignment.  The seminar will describe a stereoselective synthesis of the fully functionalized GHIJ ring fragment of gambieric acids A�D. Furthermore, the stereodivergent nature of our strategy provides access to both the original 1  and the revised structure 2  of the gambieric acids, which provides further support the absolute configuration of these important polycyclic structures.

Stereoselective synthesis of the fully functionalized GHIJ ring fragment of gambieric acids

244th National Meeting (2012)

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