Asymmetric total synthesis of (+)-K01-0509 B: determination of absolute configuration.
K01-0509 B is a novel natural product which contains a carbamoylated cyclic guanidine. Our asymmetric total synthesis features a Sharpless asymmetric epoxidation and a stereocontrolled construction of the cyclic guanidine via an asymmetric nitroaldol reaction, followed by intramolecular SN2 cyclization. These reactions allowed the cyclic guanidine and the adjacent hydroxy group to be assembled, facilitating the asymmetric total synthesis and determination of the absolute stereochemistry of K01-0509 B. [reaction: see text].
Tsuchiya
Satoshi
S
Kitasato Institute for Life Sciences, Graduate School of Infection Control Sciences, Minato-ku, Tokyo 108-8641, Japan.
Sunazuka
Toshiaki
T
Hirose
Tomoyasu
T
Mori
Ryuma
R
Tanaka
Toshiaki
T
Iwatsuki
Masato
M
Omura
Satoshi
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis; D004983:Ethanolamines; D006146:Guanidines / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry / Q000378:metabolism
D000900:Anti-Bacterial Agents; D004852:Epoxy Compounds; D004983:Ethanolamines; D006146:Guanidines; C522752:K01-0509 B; D003035:Cobalt; C025342:RP333