Total synthesis of the duocarmycins.
The total synthesis of (+)-duocarmycin A and SA through a common indoline intermediate is described. The key reactions include selective lithiation of a 2,6-dibromoiodobenzene derivative and diastereoselective addition to a chiral nitroalkene, copper-mediated aryl amination, and addition of aryllithium to azlactones.
Yamada
Ken
K
Graduate School of Pharmaceutical Sciences, University of Tokyo, Bunkyo-ku, Tokyo 113-0033, Japan.
Kurokawa
Toshiki
T
Tokuyama
Hidetoshi
H
Fukuyama
Tohru
T
D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D000080890:Duocarmycins; D007211:Indoles; D011758:Pyrroles / Q000138:chemical synthesis*; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D000903:Antibiotics, Antineoplastic; D000080890:Duocarmycins; D007211:Indoles; D011758:Pyrroles; D011760:Pyrrolidinones; C066098:duocarmycin SA; C058289:duocarmycin A