Abstract
The tetracyclic ketone 17, which possesses a framework closely related to phorbol, has been prepared in enantiomerically pure condition. Condensation of the dichlorocerate derived from 3 with 2-chlorocyclohexanone leads to chlorohydrins 4 and 5 in a 1:1 ratio. Treatment of 5 with excess vinylmagnesium bromide delivers 7, thereby setting the stage for anionic oxy-Cope rearrangement to 9. Epoxidation of 9 and base-promoted cyclization of the α-isomer ( 15) under kinetically controlled conditions eventuates in the formation of 17. A companion set of reactions was performed on 4 with the result that hemiketal 11 is formed following transannular ring closure. Lastly, one of the first intramolecularly competitive anionic oxy-Cope rearrangements is described.
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