Synthesis of the bicyclo [3.2. 0] ring systems from 4-allylcyclobutenones. Intramolecular ketene/alkene cycloadditions

SL Xu, H Xia, HW Moore

Index: Xu, Simon L.; Xia, Haiji; Moore, Harold W. Journal of Organic Chemistry, 1991 , vol. 56, # 21 p. 6094 - 6103

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Citation Number: 29

Abstract

A general synthesis of bicyclo [3.2. 0] heptenones from 4-allylcyclobutenones is described. The rearrangement is envisaged to involve an electrocyclic ring opening of the cyclobutenone and subsequent intramolecular 2+ 2 cycloaddition of the resulting vinylketene to the nonconjugated allylic alkene moiety. This method is particularly suitable for the synthesis of highly substituted derivatives since the regiochemistry of the ...