Isolation, Synthesis, and Semisynthesis of Amaryllidaceae Constituents from Narcissus and Galanthus sp.: De Novo Total Synthesis of 2- epi-Narciclasine
| Autor: | David K. Liscombe, James McNulty, Suresh Borra, Christine J. Kempthorne, Ringaile Lapinskaite, Tomas Hudlicky |
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| Rok vydání: | 2018 |
| Předmět: |
Stereochemistry
Narciclasine Pharmaceutical Science 010402 general chemistry 01 natural sciences Plant Roots Analytical Chemistry chemistry.chemical_compound Alkaloids Drug Discovery Pharmacology Natural product biology Galanthus 010405 organic chemistry Chemistry Alkaloid Organic Chemistry Amaryllidaceae Total synthesis Narcissus Phenanthrenes biology.organism_classification Semisynthesis 0104 chemical sciences Phenanthridines Complementary and alternative medicine Amaryllidaceae Alkaloids Molecular Medicine Epimer Oxidation-Reduction |
| Zdroj: | Journal of natural products. 81(6) |
| ISSN: | 1520-6025 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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