Explorations of stemona alkaloid-inspired analogues: skeletal modification and functional group diversification |
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Authors: | Frankowski Kevin J Neuenswander Benjamin Aubé Jeffrey |
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Affiliation: | Department of Medicinal Chemistry and Center for Chemical Methodologies and Library Development, University of Kansas, Malott Hall, 1251 Wescoe Hall Drive, Lawrence, Kansas 66045-7582, USA. |
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Abstract: | A tandem Diels-Alder/Schmidt reaction provided an efficient route for the exploration of unnatural Stemona alkaloid analogues. Thus, a series of tricyclic scaffolds were efficiently prepared and then elaborated into seven sets of functionalized analogues. These derivatives incorporated appended heterocycles, such as indoles and quinolines, or other diversity-incorporating moieties such as carbamates and amines. Both the scaffold-generation sequence and the diversification steps could be manipulated to provide regio- and diastereochemically pure products. |
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