title: Total synthesis and cytotoxicity of haterumalides NA and B and their artificial analogues.
abstract: The total synthesis of haterumalides NA and B, potent cytotoxic marine macrolides, was achieved by using B-alkyl Suzuki-Miyaura coupling and Nozaki-Hiyama-Kishi coupling as key steps. Compared to our first-generation approach for ent-haterumalide NA methyl ester, this second-generation synthesis yielded much more of the key intermediate. This synthesis established the relative stereochemistry of haterumalide B. Furthermore, the structure-cytotoxicity relationships of haterumalides were investigated. The combination of macrolide and side chain parts proved to be important to the cytotoxicity.
authors.affiliation: Department of Chemistry, Graduate School of Pure and Applied Sciences, and Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Ibaraki 305-8571, Japan.
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: Ichiro
authors.initials: I
authors.lastname: Hayakawa
authors.forename: Hideo
authors.initials: H
authors.lastname: Kigoshi