Total synthesis of a novel tetracyclic alkaloid, cassiarin F from the flowers of Cassia siamea. 2011

Jun Deguchi, and Tomoe Hirahara, and Shiori Oshimi, and Yusuke Hirasawa, and Wiwied Ekasari, and Osamu Shirota, and Toshio Honda, and Hiroshi Morita
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Tokyo 142-8501, Japan.

A novel alkaloid, cassiarin F (1), which showed potent antiplasmodial activity against Plasmodium falciparum in vitro, was isolated from the flowers of Cassia siamea, and its structure was elucidated on the basis of 2D NMR analyses. A total synthesis of 1 was also achieved by employing the Suzuki coupling constructing biaryl unit, nucleophilic aromatic substitution, and Houben-Hoesch type ring construction as key steps.

UI MeSH Term Description Entries
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D002366 Cassia A plant genus of the family FABACEAE. Many species of this genus, including the medicinal C. senna and C. angustifolia, have been reclassified into the Senna genus (SENNA PLANT) and some to CHAMAECRISTA. Indian Laburnum,Cassia fistula,Cassia fistulas,Cassias,Indian Laburnums,Laburnum, Indian,Laburnums, Indian,fistulas, Cassia
D006576 Heterocyclic Compounds, 4 or More Rings A class of heterocyclic compounds that include four or more fused rings. Both aromatic or non-aromatic ring structures are included in this category. Heterocyclic Compounds with 4 or More Rings,Five Ring Heterocyclic Compounds,Four Ring Heterocyclic Compounds,Fused Heterocyclic Compounds, Five-Ring,Fused Heterocyclic Compounds, Four-Ring,Heterocyclic Compounds with Four or More Rings,Heterocyclic Compounds, 4-Ring,Heterocyclic Compounds, 5-Ring,Heterocyclic Cpds, 4 Ring,Heterocyclic Cpds, 4 or More Rings,Heterocyclic Cpds, 5 Ring,4-Ring Heterocyclic Compounds,5-Ring Heterocyclic Compounds,Fused Heterocyclic Compounds, Five Ring,Fused Heterocyclic Compounds, Four Ring,Heterocyclic Compounds, 4 Ring,Heterocyclic Compounds, 5 Ring
D000470 Alkaloids Organic nitrogenous bases. Many alkaloids of medical importance occur in the animal and vegetable kingdoms, and some have been synthesized. (Grant & Hackh's Chemical Dictionary, 5th ed) Alkaloid,Plant Alkaloid,Plant Alkaloids,Alkaloid, Plant,Alkaloids, Plant
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D035264 Flowers The reproductive organs of plants. Blooms, Plant,Blossoms,Pistil,Plant Style,Anther, Plant,Carpal, Plant,Carpals, Plant,Filament, Flower,Flower Filament,Ovary, Plant,Petals, Plant,Plant Anther,Plant Calyx,Plant Carpals,Plant Corolla,Plant Ovary,Plant Petals,Plant Sepals,Plant Stamen,Plant Stigma,Sepals, Plant,Stamen, Plant,Stigma, Plant,Style, Plant,Anthers, Plant,Bloom, Plant,Blossom,Calyx, Plant,Calyxs, Plant,Corolla, Plant,Corollas, Plant,Filaments, Flower,Flower,Flower Filaments,Ovaries, Plant,Petal, Plant,Pistils,Plant Anthers,Plant Bloom,Plant Blooms,Plant Calyxs,Plant Carpal,Plant Corollas,Plant Ovaries,Plant Petal,Plant Sepal,Plant Stamens,Plant Stigmas,Plant Styles,Sepal, Plant,Stamens, Plant,Stigmas, Plant,Styles, Plant

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