Ring size in epoxynitrile cyclization. General synthesis of functionally substituted cyclobutanes. Application to (+-)-grandisol

G Stork, JF Cohen

Index: Stork,G.; Cohen,J.F. Journal of the American Chemical Society, 1974 , vol. 96, # 16 p. 5270 - 5272

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Citation Number: 167

Abstract

XV XVI its epimer (cyano cis to methylcarbinol) was-95: 5. The formation of the less stable isomer with the two larger groups cis to each other emphasizes again the lower energy of the transition state XII. The particular effectiveness of the lithium salt is presumably the result of magnifying interactions in a tight transition state. Reduction of the cyano group (diisobutylaluminum hydride) then gave hydroxy aldehyde XVIIj (52 z from the epoxide XV ...