title: Schizostatin, a novel squalene synthase inhibitor produced by the mushroom, Schizophyllum commune. II. Structure elucidation and total synthesis.
abstract: Schizostatin (1) has been isolated as a potent and selective inhibitor of squalene synthase. Its structure has been determined using spectroscopic methods: the compound is shown to be a diterpenoid which has a trans-dicarboxylic acid moiety. Total synthesis of schizostatin (1) was achieved by the highly regio- and stereoselective coupling reaction of an allylic bromide with a barium reagent. The Z-isomer 16 was also prepared using the stereoselective syn-addition of an organocopper reagent to acetylenedicarboxylate.
authors.affiliation: Exploratory Chemistry Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
authors.forename: H
authors.initials: H
authors.lastname: Kogen
authors.forename: K
authors.initials: K
authors.lastname: Tago
authors.forename: S
authors.initials: S
authors.lastname: Kaneko
authors.forename: K
authors.initials: K
authors.lastname: Hamano
authors.forename: K
authors.initials: K
authors.lastname: Onodera
authors.forename: H
authors.initials: H
authors.lastname: Haruyama
authors.forename: K
authors.initials: K
authors.lastname: Minagawa
authors.forename: T
authors.initials: T
authors.lastname: Kinoshita
authors.forename: T
authors.initials: T
authors.lastname: Ishikawa
authors.forename: T
authors.initials: T
authors.lastname: Tanimoto
authors.forename: Y
authors.initials: Y
authors.lastname: Tsujita
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D013186:Farnesyl-Diphosphate Farnesyltransferase / Q000037:antagonists & inhibitors*; D005227:Fatty Acids / Q000138:chemical synthesis / Q000737:chemistry*; D005650:Fumarates / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012567:Schizophyllum / Q000378:metabolism; D016339:Spectrometry, Mass, Fast Atom Bombardment
chemical_list: D004791:Enzyme Inhibitors; D005227:Fatty Acids; D005650:Fumarates; C101437:schizostatin; D013186:Farnesyl-Diphosphate Farnesyltransferase