Total synthesis of (-)-borrelidin.
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]
Nagamitsu
Tohru
T
School of Pharmaceutical Science, Kitasato University, Kitasato Institute for Life Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.
Takano
Daisuke
D
Fukuda
Takeo
T
Otoguro
Kazuhiko
K
Kuwajima
Isao
I
Harigaya
Yoshihiro
Y
Omura
Satoshi
S
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
D000900:Anti-Bacterial Agents; D000962:Antimalarials; D005233:Fatty Alcohols; C005066:borrelidin