Novel Oxidative Rearrangement Product of the First trans,cis,cis,cis-[5.5.5.5]Fenestrane Derivative

The structure of rel-(4S,6R,9S,11S)-1-hydroxy-16-methyl-14-oxapentacyclo[7.4.3.0^4,15.0^11,15.0^6,16]hexadeca-7-ene, C₁₆H₂₂O₂, (IV), has been determined. This study thus establishes compound (III), the precursor of (IV), as the first trans,cis,cis,cis[5.5.5.5]fenestrane. The geometry around the central quaternary C atom of (IV) shows relatively little distortion. The C=C bond in the cyclopentene subunit is slightly shorter [1.305 (4) Å] than normal. Similarly, small departures from normal are seen in several C-C single bonds.

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