Stereoselective synthesis and cyclisation of the acyclic precursor to auripyrone A and B |
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Authors: | Michael V Perkins Rebecca A Sampson John Joannou Max R Taylor |
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Institution: | School of Chemistry, Physics and Earth Sciences, Flinders University, GPO Box 2100, 5001 South Australia, Australia |
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Abstract: | The acyclic precursor to the auripyrones has been synthesized by a stereoselective aldol strategy. This compound fails to undergo cyclisation to form the spiroacetal dihydropyrone ring system found in auripyrone A and B; instead, it forms a dihydropyrone ring by cyclisation of the C11 hydroxyl onto the C15 carbonyl with subsequent dehydration. In contrast, a model compound was prepared and shown to cyclise to both the spiroacetal dihydropyrone ring system and the dihydropyrone ring. |
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