title: Total synthesis of borrelidin.
abstract: The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to the samarium(II) iodide-mediated intramolecular Reformatsky-type reaction as the most efficient synthetic approach. The two key segments were synthesized through regioselective methylation, directed hydrogenation, stereoselective Reformatsky-type reaction, and MgBr2.Et2O-mediated chelation-controlled allylation.
authors.affiliation: School of Pharmacy, 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: Kaori
authors.initials: K
authors.lastname: Marumoto
authors.forename: Takeo
authors.initials: T
authors.lastname: Fukuda
authors.forename: Kentaro
authors.initials: K
authors.lastname: Furuya
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Otoguro
authors.forename: Kazuyoshi
authors.initials: K
authors.lastname: Takeda
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: D003500:Cyclization; D005233:Fatty Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005233:Fatty Alcohols; C005066:borrelidin