title: Total synthesis of 13-demethyllyngbyaloside B.
abstract: Total synthesis of 13-demethyllyngbyaloside B, an unnatural analogue of a marine macrolide glycoside lyngbyaloside B, has been achieved. The 14-membered macrocyclic backbone was constructed in a convergent manner via esterification and ring-closing metathesis. The bromodiene side chain was introduced by means of a Stille-type reaction and a subsequent bromodesilylation. Finally, the rhamnopyranose unit was stereoselectively introduced by glycosylation under Schmidt conditions.
authors.affiliation: Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan. hfuwa@m.tohoku.ac.jp
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Fuwa
authors.forename: Naoya
authors.initials: N
authors.lastname: Yamagata
authors.forename: Asami
authors.initials: A
authors.lastname: Saito
authors.forename: Makoto
authors.initials: M
authors.lastname: Sasaki
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C583477:13-demethyllyngbyaloside B; D000900:Anti-Bacterial Agents; D006842:Hydrocarbons, Brominated; D018942:Macrolides; C464989:lyngbouilloside; C473445:lyngbyaloside B