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Arborisidine and Arbornamine, Two Monoterpenoid Indole Alkaloids with New Polycyclic Carbon–Nitrogen Skeletons Derived from a Common Pericine Precursor

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    Arborisidine and Arbornamine, Two Monoterpenoid Indole Alkaloids with New Polycyclic Carbon–Nitrogen Skeletons Derived from a Common Pericine Precursor
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    † Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
    ‡ School of Pharmacy, University of Nottingham Malaysia Campus, Jalan Broga, 43500 Semenyih, Selangor, Malaysia
    *E-mail: [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2016, 18, 7, 1618–1621
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    https://doi.org/10.1021/acs.orglett.6b00478
    Published March 22, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    Two new monoterpene indole alkaloids, characterized by previously unencountered natural product skeletons, viz., arborisidine (1), incorporating indolizidine and cyclohexanone moieties fused to an indole unit, and arbornamine (2), incorporating an unprecedented 6/5/6/5/6 “arbornane” skeleton (distinct from the eburnan or tacaman skeleton), were isolated from a Malayan Kopsia arborea. The structures of the alkaloids were determined based on analysis of the NMR and MS data. Possible biogenetic pathways to these alkaloids from a common pericine precursor (3) are presented.

    Copyright © 2016 American Chemical Society

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    • Experimental procedures, 1D, 2D NMR, and HRESIMS data of compounds 1, 2, and 9, ECD data for 1, calculated free energies, and Cartesian coordinates for 2 (chair and twist-boat conformers) (PDF)

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    This article is cited by 60 publications.

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    Organic Letters

    Cite this: Org. Lett. 2016, 18, 7, 1618–1621
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.6b00478
    Published March 22, 2016
    Copyright © 2016 American Chemical Society
    Request reuse permissions

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