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    Isolation, Synthesis, and Semi-synthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De novo Total Synthesis of 2-epi-Narciclasine.

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    Name:
    Hudlicky J. Nat. Prod. Manuscr ...
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    Author
    Borra, Suresh
    Lapinskaite, Ringaile
    Kempthorne, Christine
    Liscombe, David
    McNulty, James
    Hudlicky, Tomas
    Keyword
    Amaryllidaceae constituents
    Natural product synthesis
    epi-narciclasine
    
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    URI
    http://hdl.handle.net/10464/13870
    Abstract
    An efficient protocol for the isolation of narciclasine from common Amaryllidaceae bulbs, separation from haemanthamine, and the occurrence of a trace alkaloid, 2-epi-narciclasine are reported. Attempts to convert natural narciclasine to its C-2 epimer by Mitsunobu inversion or oxidation/reduction sequences were compromised by rearrangement and aromatization processes, through which a synthesis of the alkaloid narciprimine was achieved. The methylation of the 7-hydroxy group of natural narciclasine followed by protection of the 3,4-diol function and oxidation/reduction sequence provided the target C-2 epimer. A de novo chemoenzymatic synthesis of 2-¬epi-narciclasine from m-dibromobenzene is also described. Haemanthamine and narciprimine were readily detected in the crude extracts of Narcissus and Galanthus bulbs containing narciclasine and the occurrence of 2-epi-narciclasine as a trace natural product in Galanthus sp. is reported for the first time.
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.jnatprod.8b00218
    Scopus Count
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    Chemistry

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