Convenient synthesis of 5,6,11,12,17,18- hexahydrocyclononal[1,2-b:4,5-b':7,8-b'']triindole, a novel phytoestrogen.
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.
Staub
Richard E
RE
Department of Nutritional Sciences and Toxicology, University of California, Berkeley, California 94720-3104, USA.
Bjeldanes
Leonard F
LF
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
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