title: Total synthesis of (-)-borrelidin.
abstract: The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is SmI(2)-mediated intramolecular Reformatsky-type reaction for macrocyclization after esterification between two segments. The two key segments were synthesized through chelation-controlled carbotitanation, chelation-controlled hydrogenation, stereoselective Reformatsky reaction, and MgBr(2).Et(2)O-mediated chelation-controlled allylation. [reaction: see text]
authors.affiliation: School of Pharmaceutical Science, Kitasato University, Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
authors.forename: Tohru
authors.initials: T
authors.lastname: Nagamitsu
authors.forename: Daisuke
authors.initials: D
authors.lastname: Takano
authors.forename: Takeo
authors.initials: T
authors.lastname: Fukuda
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Otoguro
authors.forename: Isao
authors.initials: I
authors.lastname: Kuwajima
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Harigaya
authors.forename: Satoshi
authors.initials: S
authors.lastname: Omura
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000962:Antimalarials / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D000962:Antimalarials; D005233:Fatty Alcohols; C005066:borrelidin