Total Synthesis of (+)‐Madangamine D |
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Authors: | Roberto Ballette Dr Maria Pérez Dr Stefano Proto Prof Dr Mercedes Amat Prof Dr Joan Bosch |
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Institution: | Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, 08028‐Barcelona (Spain) http://www.ub.edu/sintefarma/ |
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Abstract: | Madangamines are a group of bioactive marine sponge alkaloids, embodying an unprecedented diazapentacyclic skeletal type. The enantioselective total synthesis of madangamine D has been accomplished, and represents the first total synthesis of an alkaloid of the madangamine group. It involves the stereoselective construction of the diazatricyclic ABC core using a phenylglycinol‐derived lactam as the starting enantiomeric scaffold and the subsequent assembly of the peripheral macrocyclic rings. The synthesis provides, for the first time, a pure sample of madangamine D and confirms the absolute configuration of this alkaloid family. |
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Keywords: | alkaloids asymmetric synthesis macrocycles nitrogen heterocycles total synthesis |
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