As easy as ABCD: (−)-Jiadifenin was synthesized in eighteen reaction steps from 1-[(E)-(4′-bromo-2′-butenyl)oxy]-4-methoxybenzene. Key features of this synthesis include: 1) Ireland–Claisen rearrangement to produce the two contiguous quaternary centers at C5 and C6 simultaneously, 2) intramolecular Pauson–Khand reaction (IMPKR) to concurrently construct the A and B rings, and 3) [2+2] photo-cycloaddition to generate the all-carbon quaternary center at C9.
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