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Abstract
Abstract The putative common precursor to siphonarin B, baconipyrone A, baconipyrone C, and caloundrin B was prepared by an enantioselective total synthesis featuring our thiopyran route to polypropionates strategy. In the presence of imidazole, the precursor undergoes ring–chain tautomerism to afford siphonarin B that, upon treatment with alumina in hot ethanol, rearranges to baconipyrone A and baconipyrone C via a retro-Claisen reaction. The presence of caloundrin B was not detected in these (or many other) isomerization experiments. Caloundrin B was prepared by a total synthesis featuring a novel aldol coupling of enantiopure and racemic fragments and rearranges to siphonarin B in the presence of imidazole. Consequently, caloundrin B cannot be an isolation artifact and must be considered a plausible biosynthetic product from which the in vitro formation of siphonarin B, baconipyrone A, baconipyrone C can be readily explained.
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