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Free, publicly-accessible full text available August 14, 2026
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Tuccinardi, Joseph P.; Wood, John L. (, Journal of the American Chemical Society)
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An, Jason; Jackson, III, Richard K.; Tuccinardi, Joseph P.; Wood, John L. (, Organic Letters)
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Hwang, Taehwan; Tuccinardi, Joseph P.; Beard, Alexandra A.; Jackson, Amy C.; Jung, Min J.; Wood, John L. (, Angewandte Chemie International Edition)Abstract Described herein are the first total syntheses of (±)‐dracocephalone A (1) and (±)‐dracocequinones A (4) and B (5). The synthesis was initially envisioned as proceeding through an intramolecular isobenzofuran Diels–Alder reaction, a strategy that eventually evolved into a Lewis acid‐promoted spirocyclization. This highly diastereoselective transformation set the stage fortrans‐decalin formation and a late‐stage Suárez oxidation that produced a [3.2.1] oxabicycle suited for conversion to1. Brønsted acid‐mediated aromatization, followed by a series of carefully choreographed oxidations, allowed for rearrangement to a [2.2.2] oxabicycle poised for conversion to4and5.more » « less
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