title: Total synthesis of amphidinolide Y by formation of trisubstituted (E)-double bond via ring-closing metathesis of densely functionalized alkenes.
abstract: Amphidinolide Y, a 17-membered cytotoxic macrolide isolated from marine dinoflagellates, has been synthesized via ring-closing metathesis to assemble the congested trisubstituted (E)-double bond. The seco precursor was prepared from readily available chiral synthons with the tetrahydrofuran ring formed via 5-endo epoxide ring-opening cyclization. It was found that the C6-keto seco substrate showed higher reactivity toward Grubbs' second generation catalyst while Schrock's Mo catalyst was completely inactive for formation of the macrocycle.
authors.affiliation: Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, China.
authors.forename: Jian
authors.initials: J
authors.lastname: Jin
authors.forename: Yile
authors.initials: Y
authors.lastname: Chen
authors.forename: Yannian
authors.initials: Y
authors.lastname: Li
authors.forename: Jinlong
authors.initials: J
authors.lastname: Wu
authors.forename: Wei-Min
authors.initials: WM
authors.lastname: Dai