Total synthesis of (+)-yatakemycin.
A convergent total synthesis of (+)-yatakemycin was accomplished in a 20-step sequence in an overall yield of 13%. The synthesis features the regioselective ring opening of (S)-epichlorohydrin with 2,6-dibromophenyllithium species, the mild copper-mediated aryl amination utilizing the combination of CuI and CsOAc, and the efficient deprotection of benzyl groups of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene.
Okano
Kentaro
K
Graduate School of Pharmaceutical Sciences, University of Tokyo, PRESTO, Japan Science and Technology Agency, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Tokuyama
Hidetoshi
H
Fukuyama
Tohru
T
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D000080890:Duocarmycins; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D000080890:Duocarmycins; D007211:Indoles; D011758:Pyrroles; C474180:yatakemycin