Total synthesis of borrelidin.
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.
Nagamitsu
Tohru
T
School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
Takano
Daisuke
D
Marumoto
Kaori
K
Fukuda
Takeo
T
Furuya
Kentaro
K
Otoguro
Kazuhiko
K
Takeda
Kazuyoshi
K
Kuwajima
Isao
I
Harigaya
Yoshihiro
Y
Omura
Satoshi
S
D003500:Cyclization; D005233:Fatty Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D005233:Fatty Alcohols; C005066:borrelidin