Journal of the Chemical Society. Perkin transactions I p. 3242 - 3249 (1981)
Update date:2022-08-04
Topics: Characterization Purification Final steps Stereochemistry Control Starting Materials Purification and Analysis Ring Expansion Functional Group Manipulations Oxidation and Reduction Further Elaboration
Bateson, John H.
Baxter, Andrew J. G.
Roberts, Patricia M.
Smale, Terence C.
Southgate, Robert
4-Allylazetidin-2-one, prepared from penta-1,4-diene and chlorosulphonyl isocyanate, has been used to synthesise the parent 7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate system of the naturally occurring olivanic acids, using an intramolecular Wittig reaction to construct the 2,3-double bond.Cyclisation of ketones derived from the 4-allyl grouping produced 3-substituted derivatives, while use of the azetidin-2-one prepared from hexa-1,5-diene and chlorosulphonyl isocyanate has given the homologous 8-oxo-1-azabicyclo<4.2.0>oct-2-ene system.
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