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Bioinspired synthesis of pentacyclic onocerane triterpenoids

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Abstract

The first chemical synthesis of pentacyclic onocerane triterpenoids has been achieved. A putative biomimetic tricyclization cascade is employed to forge a fused decalin-/oxepane ring system. The synthetic route proceeds to (+)-cupacinoxepin in seven steps and to (+)-onoceranoxide in eight steps in the longest linear sequence, when starting from geranyl chloride and (+)-sclareolide. The bioinspired epoxypolyene cyclization is supported by computational and enzymatic studies.

Graphical abstract: Bioinspired synthesis of pentacyclic onocerane triterpenoids

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Publication details

The article was received on 06 Sep 2017, accepted on 14 Oct 2017 and first published on 16 Oct 2017


Article type: Edge Article
DOI: 10.1039/C7SC03903D
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Bioinspired synthesis of pentacyclic onocerane triterpenoids

    F. Bartels, Y. J. Hong, D. Ueda, M. Weber, T. Sato, D. J. Tantillo and M. Christmann, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C7SC03903D

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