A Synthetic Entry into the Taiwaniaquinoids Based on a Biogenetic Hypothesis: Total Synthesis of (-)-Taiwaniaquinone H

(Chemical Equation Presented) Less carbon: Following a biogenetic proposal, the unusual 6-5-6 carbon skeleton of C19 taiwaniaquinoids was obtained by an intramolecular benzilic acid rearrangement from a C20 precur-sor. A protecting-group-free total synthesis then allowed for the preparation of (-)-taiwaniaquinone H (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.