Macrocyclic lactam synthesis via a ring expansion reaction: construction of the cripowellin skeleton.
[reaction: see text] The cripowellin ring skeleton, a macrocyclic [2.3.5]-bicyclic ketolactam, was smoothly generated via construction of a spiro(benzazepin-cyclohexane-1,3-dione) employing oxidative cyclization as a key step and a subsequent ring expansion reaction.
Moon
Bongjin
B
Department of Chemistry, Sogang University, Seoul 121-742, Korea. bjmoon@ccs.sogang.ac.kr
Han
Sangbae
S
Yoon
Yeojin
Y
Kwon
Hyejin
H
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007202:Indicators and Reagents; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry
D047151:Amaryllidaceae Alkaloids; D007202:Indicators and Reagents; D047029:Lactams, Macrocyclic; C506143:cripowellin A; C506144:cripowellin B