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Exploring Symmetry-Based Logic for a Synthesis of Palau’amine

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journal contribution
posted on 21.08.2009, 00:00 by Qingyi Li, Paul Hurley, Hui Ding, Andrew G. Roberts, Radha Akella, Patrick G. Harran
A synthetic approach to palau’amine is described that exploits veiled symmetry in the structure. Bis-alkylidenes i have been prepared and found susceptible to halogenative desymmetrization using t-BuOCl. This oxidation forms the imbedded spirocyclopentane motif observed in the natural product. A host of atypical reactions and processes developed during these studies are discussed, as are plans for completing total syntheses of this compound class.