Total Syntheses of (±)‐Dracocephalone A and (±)‐Dracocequinones A and B
Taehwan Hwang, Joseph P. Tuccinardi, Alexandra A. Beard, Amy C. Jackson, Min J. Jung, John L. Wood
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Source: Crossref
Published: Oct 14, 2022
DOI: 10.1002/ange.202210821
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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 for trans ‐decalin formation and a late‐stage Suárez oxidation that produced a [3.2.1] oxabicycle suited for conversion to 1 . Brønsted acid‐mediated aromatization, followed by a series of carefully choreographed oxidations, allowed for rearrangement to a [2.2.2] oxabicycle poised for conversion to 4 and 5 .
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