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Highly Substituted Oxabicyclic Derivatives from Furan: Synthesis of (±)-Platensimycin

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journal contribution
posted on 06.05.2011, 00:00 by E. Zachary Oblak, Dennis L. Wright
A stereocontrolled approach to a key platensimycin intermediate was achieved from a commercially available furylcarboxylate. Key to our approach is the highly efficient formal [4 + 3] cyclocondensation of a substituted furan with tetrabromocyclopropene along with an intramolecular γ-alkylation to construct the final ring of the caged intermediate.