title: Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen.
abstract: An efficient one-pot synthesis is described of 5,6,11,12,17,18-hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole (CTr), a potent estrogen agonist from food plants. For the procedure, gramine is treated with dimethyl sulfate and sodium in ethanol at room temperature. Quenching of the reaction with water and workup of the product provides CTr in approximately 75% yield.
authors.affiliation: Department of Nutritional Sciences and Toxicology, University of California, Berkeley, California 94720-3104, USA.
authors.forename: Richard E
authors.initials: RE
authors.lastname: Staub
authors.forename: Leonard F
authors.initials: LF
authors.lastname: Bjeldanes
mesh_terms: D001937:Brassica / Q000737:chemistry; D002384:Catalysis; D004968:Estrogens, Non-Steroidal / Q000032:analysis / Q000138:chemical synthesis*; D007211:Indoles / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D007529:Isoflavones; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D048789:Phytoestrogens; D028321:Plant Preparations; D011960:Receptors, Estrogen / Q000819:agonists*; D013329:Structure-Activity Relationship; D013696:Temperature; D014867:Water
chemical_list: D004968:Estrogens, Non-Steroidal; D007211:Indoles; D007529:Isoflavones; D048789:Phytoestrogens; D028321:Plant Preparations; D011960:Receptors, Estrogen; D014867:Water; C074140:5,6,11,12,17,18-hexahydrocyclononatriindole; C016517:indole-3-carbinol