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dc.contributor.authorBorra, Suresh
dc.contributor.authorLapinskaite, Ringaile
dc.contributor.authorKempthorne, Christine
dc.contributor.authorLiscombe, David
dc.contributor.authorMcNulty, James
dc.contributor.authorHudlicky, Tomas
dc.date.accessioned2019-01-03T14:26:32Z
dc.date.available2019-01-03T14:26:32Z
dc.date.issued2018-05-22
dc.identifier.citationJ. Nat. Prod., 2018, 81 (6), 1451–1459en_US
dc.identifier.issn1520-6025
dc.identifier.urihttp://hdl.handle.net/10464/13870
dc.description.abstractAn 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.en_US
dc.description.sponsorshipNSERC Idea to Innovation - I2IPJ-470630-14 NSERC Discovery Grant - RGPIN-2018-03723en_US
dc.language.isoenen_US
dc.publisherACSen_US
dc.subjectAmaryllidaceae constituentsen_US
dc.subjectNatural product synthesisen_US
dc.subjectepi-narciclasineen_US
dc.titleIsolation, Synthesis, and Semi-synthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De novo Total Synthesis of 2-epi-Narciclasine.en_US
dc.typeArticleen_US
dc.identifier.doi10.1021/acs.jnatprod.8b00218


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