| Abstract
| - Diol 2, derived in two steps from p-benzoquinone, was converted to epoxy alcohol 3. The latterwas resolved with crude Candida rugosa lipase in isopropenyl acetate/toluene to give acetate (−)-4and residual alcohol (+)-3. Oxirane ring opening reactions of 3 and the corresponding acetate andTBDMS derivatives with a variety of nucleophiles gave diastereomerically pure 3,4,5,6-tetrasubstituted cyclohexene derivatives of type 6. X-ray crystal structures were obtained on compounds6e, 6m and the diacetate prepared from 6l. Nitrogen nucleophiles provided entry in variousaziridines 10. Pd(0)-catalyzed nucleophilic additions to substrate 5 cleanly provided the diastereomeric pattern of type 11. trans-5,6-Disubstituted cyclohexadienes 13 were obtained by an unusualsyn-reductive elimination on bromocarbonates 12 utilizing Pd or Zn.
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