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Synthesis of the ABC Substructure of Brevenal by Sequential exo‑Mode Oxacyclizations of Acyclic Polyene Precursors

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journal contribution
posted on 30.10.2017, 15:22 by Jessica A. Hurtak, Frank E. McDonald
Exploratory studies on the sequential exo-mode oxacyclizations of acyclic polyene precursors have provided a substantial substructure of brevenal, including the fused tricyclic polyether with stereochemical patterns consistent with the AB and BC ring fusions. The synthesis of acyclic substrates featured two variations of Cr­(II)/Ni­(II) couplings for preparing 1,1-disubstituted allylic alcohols. A sequence of iodine-promoted cycloetherification, base-promoted intramolecular conjugate addition, and mercury-promoted cycloetherification produced the tricyclic substructure.

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