Synthetic study toward ecteinascidin 743: concise construction of the diazabicyclo[3.3.1]nonane skeleton and assembly of the pentacyclic core.
Synthesis of the pentacyclic core of ecteinascidin 743 is described. This synthesis features concise construction of the diazabicyclo[3.3.1]nonane skeleton using gold(I)-catalyzed one-pot keto amide formation, acid-promoted enamide formation, and oxidative Friedel-Crafts cyclization as the key steps.
Enomoto
Taro
T
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan. takemoto@pharm.kyoto-u.ac.jp
Yasui
Yoshizumi
Y
Takemoto
Yoshiji
Y
D001688:Biological Products / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010649:Phenylalanine / Q000138:chemical synthesis* / Q000737:chemistry; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D013237:Stereoisomerism; D044005:Tetrahydroisoquinolines / Q000737:chemistry*
D001688:Biological Products; D019086:Bridged Bicyclo Compounds, Heterocyclic; D011084:Polycyclic Aromatic Hydrocarbons; D044005:Tetrahydroisoquinolines; D010649:Phenylalanine