Daphcalycine,a novel heptacycle fused ring system alkaloid from Daphniphyllum calycinum |
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Authors: | Jossang Akino El Bitar Hoda Pham Van Cuong Sévenet Thierry |
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Institution: | Laboratoire de Chimie des Substances Naturelles, ESA 8041 CNRS, Muséum National d'Histoire Naturelle, 63 rue Buffon 75005 PARIS, France. jossang@mnhn.fr |
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Abstract: | A novel Daphniphyllum alkaloid, daphcalycine (1), was isolated together with known daphnicyclidin D (2) from the stem bark of Daphniphyllum calycinum. The highly condensed polycyclic structure, established by spectral analysis, possessed an unusual framework: a central quinuclidine like tricycle produced by fusion of a piperidine, a tetrahydropyran, and an oxazine ring in turn condensed to surrounding three penta-, one hexa-, and one hepta-membered rings. The relative configuration of 11 carbon stereocenters of 1 was elucidated on the basis of NOESY. |
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