Synthetic studies of cephalandole alkaloids and the revised structure of cephalandole A.
A synthesis of the originally proposed 2-(1 H-indol-3-yl)-4 H-3,1-benzoxazin-4-one structure of the alkaloid cephalandole A (1) led to a structural revision, and the isolated natural product has now been identified as the previously known compound 3-(1 H-indol-3-yl)-2 H-1,4-benzoxazin-2-one (7). The structural assignment was corroborated by detailed NMR studies. A short synthesis of the related natural compound cephalandole B (2) has also been performed, confirming its structure. In addition some chemical transformations, involving, for example, the related synthetic molecule 2-(1 H-indol-3-yl)-3 H-quinazolin-4-one (9), are presented.
Mason
Jeffrey J
JJ
Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park, SE-141 57 Huddinge, Sweden.
Bergman
Jan
J
Janosik
Tomasz
T
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D029595:Orchidaceae / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
D000470:Alkaloids; D048588:Benzoxazines; D007211:Indoles; C533328:cephalandole A