title: Total Synthesis of Mycalolides A and B through Olefin Metathesis.
abstract: An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1-C19 trisoxazole and C20-C35 side-chain segments through the use of olefin metathesis and esterification as well as Julia-Kocienski olefination and enamide formation as key steps.
authors.affiliation: Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan). mkita@chem.tsukuba.ac.jp.
authors.forename: Masaki
authors.initials: M
authors.lastname: Kita
authors.affiliation: Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan).
authors.forename: Hirotaka
authors.initials: H
authors.lastname: Oka
authors.affiliation: Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan).
authors.forename: Akihiro
authors.initials: A
authors.lastname: Usui
authors.affiliation: Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan).
authors.forename: Tomoya
authors.initials: T
authors.lastname: Ishitsuka
authors.affiliation: Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan).
authors.forename: Yuzo
authors.initials: Y
authors.lastname: Mogi
authors.affiliation: Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan).
authors.forename: Hidekazu
authors.initials: H
authors.lastname: Watanabe
authors.affiliation: Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan).
authors.forename: Masaki
authors.initials: M
authors.lastname: Tsunoda
authors.affiliation: Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan). kigoshi@chem.tsukuba.ac.jp.
authors.forename: Hideo
authors.initials: H
authors.lastname: Kigoshi
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D008387:Marine Toxins; D008968:Molecular Conformation; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D008387:Marine Toxins; D010080:Oxazoles; C553072:mycalolide A; C080978:mycalolide B
keywords: esterification; macrolactonization; natural products; olefin metathesis; total synthesis