title: Second-generation total synthesis of haterumalide NA using B-alkyl Suzuki-Miyaura coupling.
abstract: Second-generation total synthesis of haterumalide NA, a potent cytotoxic marine macrolide, was achieved by using B-alkyl Suzuki-Miyaura coupling and Nozaki-Hiyama-Kishi coupling as key steps (1.2% in 33 steps). Compared to our first-generation approach, the second-generation synthesis is much improved in the yield of key intermediate.
authors.affiliation: Department of Chemistry, Graduate School of Pure and Applied Sciences, Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Ibaraki, Japan.
authors.forename: Ichiro
authors.initials: I
authors.lastname: Hayakawa
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Ueda
authors.forename: Masashi
authors.initials: M
authors.lastname: Yamaura
authors.forename: Yoichi
authors.initials: Y
authors.lastname: Ikeda
authors.forename: Yuta
authors.initials: Y
authors.lastname: Suzuki
authors.forename: Kensaku
authors.initials: K
authors.lastname: Yoshizato
authors.forename: Hideo
authors.initials: H
authors.lastname: Kigoshi
mesh_terms: D000818:Animals; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins / Q000737:chemistry; D011161:Porifera / Q000737:chemistry
chemical_list: D018942:Macrolides; D008387:Marine Toxins