title: Synthesis of (±)-terpendole E.
abstract: The first synthesis of the racemate of terpendole E, a specific inhibitor of the mitotic kinesin Eg5, has been achieved from a known tricyclic dihydroxy ketone by a 13-step sequence that involves diastereoselective installation of its C3 quaternary stereocenter via a cyclopropyl ketone intermediate and Pd-mediated two-step construction of the indole ring moiety as the key transformations.
authors.affiliation: a Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science , Tohoku University , Sendai , Japan.
authors.forename: Takaaki
authors.initials: T
authors.lastname: Teranishi
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Murokawa
authors.forename: Masaru
authors.initials: M
authors.lastname: Enomoto
authors.forename: Shigefumi
authors.initials: S
authors.lastname: Kuwahara
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D007659:Ketones / Q000737:chemistry*; D016547:Kinesins / Q000037:antagonists & inhibitors / Q000378:metabolism; D008870:Microtubules / Q000187:drug effects / Q000378:metabolism; D008938:Mitosis / Q000187:drug effects; D008941:Spindle Apparatus / Q000187:drug effects; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D004791:Enzyme Inhibitors; D007211:Indoles; C470243:KIF11 protein, human; D007659:Ketones; C477863:terpendole E; D016547:Kinesins
keywords: antimitotic; indole diterpene; kinesin spindle protein; terpendole; total synthesis