Enantioselective Total Synthesis of the Reported Structures of (-)-9-epi-Presilphiperfolan-1-ol and (-)-Presilphiperfolan-1-ol: Structural Confirmation and Reassignment and Biosynthetic Insights |
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| Authors: | Allen Y Hong Brian M Stoltz |
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| Affiliation: | Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Blvd, MC 101-20, Pasadena, CA 91125 (USA). |
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| Abstract: | When epi isn't! The first total synthesis of the reported structures of 9-epi-presilphiperfolan-1-ol and presilphiperfolan-1-ol has been achieved. Key steps are a catalytic asymmetric alkylation of a novel diene-containing electrophile followed by a two-carbon ring contraction and an intramolecular Diels-Alder cycloaddition to form the stereochemically dense tricyclic core. The synthetic work has resulted in the structural revision of presilphiperfolan-1-ol. |
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| Keywords: | asymmetric catalysis natural products structure determination terpenoids total synthesis |
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