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Bioorg Med Chem Lett. 2012 Aug 15;22(16):5253-6. doi: 10.1016/j.bmcl.2012.06.052. Epub 2012 Jun 23.

Non-canonical regioisomerizations and a 'Diels-Alderase' are likely essential in the biosynthesis of spiculoic acid A.

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Department of Chemistry, Syracuse University, Syracuse, NY 13244, USA.


The regiochemistry of dehydration and cyclization steps of the linear biosynthetic precursor of the polyketide natural product Spiculoic acid A (1) were examined. Herein we describe the synthesis of polyene-containing aldehyde 21, a counterpart to the metabolite's putative polyketide intermediate and demonstrate its inability to undergo facile IMDA chemistry. These results suggest the involvement of a non-canonical regioisomerization in the biosynthesis of 1, and that the IMDA reaction is likely enzyme-catalyzed.

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