The Total Synthesis of (−)‐Nitidasin |
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Authors: | Dr. Daniel T. Hog Dipl.‐Chem. Florian M. E. Huber Dr. Peter Mayer Prof. Dr. Dirk Trauner |
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Affiliation: | Department of Chemistry and Center for Integrated Protein Science, Ludwig‐Maximilians‐Universit?t München, Butenandtstr. 5–13, 81377 München (Germany) http://www.cup.uni‐muenchen.de/oc/trauner/ |
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Abstract: | Nitidasin is a pentacyclic sesterterpenoid with a rare 5‐8‐6‐5 carbon skeleton that was isolated from the Peruvian folk medicine “Hercampuri”. It belongs to a small class of sesterterpenoids that feature an isopropyl trans‐hydrindane moiety fused to a variety of other ring systems. As a first installment of our general approach toward these natural products, we report the total synthesis of the title compound. Our stereoselective, convergent route involves the addition of a complex alkenyl lithium compound to a trans‐hydrindanone, followed by chemoselective epoxidation, ring‐closing olefin metathesis, and redox adjustment. |
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Keywords: | ring‐closing olefin metathesis sesterterpenoids stereoselective synthesis total synthesis |
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