Total synthesis of aristolactams via a one-pot suzuki-miyaura coupling/aldol condensation cascade reaction.
A direct one-pot synthesis of phenanthrene lactams, which employs a Suzuki-Miyaura coupling/aldol condensation cascade reaction of isoindolin-1-one with 2-formylphenylboronic acid, has been developed. The approach is used to efficiently produce a number of natural aristolactams, such as aristolactam BII (cepharanone B), aristolactam BIII, aristolactam FI (piperolactam A), N-methyl piperolactam A, and sauristolactam.
Kim
Joa Kyum
JK
Center for Medicinal Chemistry, Korea Research Institute of Chemical Technology, 100 Jang-dong, Daejeon 305-600, Korea.
Kim
Young Ha
YH
Nam
Ho Tae
HT
Kim
Bum Tae
BT
Heo
Jung-Nyoung
JN
D000447:Aldehydes / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D054833:Isoindoles / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010616:Phenanthrenes / Q000138:chemical synthesis* / Q000737:chemistry; D010936:Plant Extracts / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000470:Alkaloids; D001897:Boronic Acids; D026121:Indole Alkaloids; D054833:Isoindoles; D007769:Lactams; D010616:Phenanthrenes; D010936:Plant Extracts; C487927:aristolactam BII; C457227:piperolactam A; C064673:sauristolactam; C116609:3-hydroxybutanal