Exploring symmetry-based logic for a synthesis of Palau'amine

Qingyi Li, Paul Hurley, Hui Ding, Andrew G. Roberts, Radha Akella, Patrick G. Harran

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33 Scopus citations

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)5909-5919
Number of pages11
JournalJournal of Organic Chemistry
Volume74
Issue number16
DOIs
StatePublished - Jan 1 2009

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Li, Q., Hurley, P., Ding, H., Roberts, A. G., Akella, R., & Harran, P. G. (2009). Exploring symmetry-based logic for a synthesis of Palau'amine. Journal of Organic Chemistry, 74(16), 5909-5919. https://doi.org/10.1021/jo900755r