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Exploring symmetry-based logic for a synthesis of palau'amine.

ABSTRACT: 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.

SUBMITTER: Li Q

PROVIDER: S-EPMC2888864 | biostudies-literature | 2009 Aug

REPOSITORIES: biostudies-literature

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Exploring symmetry-based logic for a synthesis of palau'amine.

Li Qingyi Q Hurley Paul P Ding Hui H Roberts Andrew G AG Akella Radha R Harran Patrick G PG

The Journal of organic chemistry 20090801 16

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. ...[more]

PMID: 19603820

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