Synthetic study of macquarimicins: highly stereoselective construction of the AB-ring system |
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| Authors: | Munakata R Ueki T Katakai H Takao K I Tadano K I |
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| Affiliation: | Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. |
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| Abstract: | The highly stereoselective synthesis of the AB-ring system of macquarimicins, a novel class of microbial metabolites with inhibitory activity for neutral sphingomyelinase, has been achieved. The present synthesis features the highly stereocontrolled construction of the cis-tetrahydroindan structure via the intramolecular Diels-Alder reaction of an (E,Z,E)-1,6,8-nonatriene derived from D-glyceraldehyde acetonide. Reaction: see text. |
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