Total Synthesis of (±)-Phomoidride D.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2018)
Abstract
Described herein is a synthetic strategy for the total synthesis of (+/-)-phomoidrideD. This highly efficient and stereoselective approach provides rapid assembly of the carbocyclic core by way of a tandem phenolic oxidation/intramolecular Diels-Alder cycloaddition. A subsequent SmI2-mediated cyclization cascade delivers an isotwistane intermediate poised for a Wharton fragmentation that unveils the requisite bicyclo[4.3.1]decene skeleton and sets the stage for synthesis completion.
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Key words
bicyclic compounds,cycloaddition,natural products,oxidation,total synthesis
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