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Olivanic Acid Analogues. Part 1. Total Synthesis of the 7-Oxo-1-azabicyclohept-2-ene-2-carboxylate System and Some Related β-Lactams

DOI: 10.1039/P19810003242

Source and publish data:

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  

Authors:

Bateson, John H.Bateson, John H.

Baxter, Andrew J. G.Baxter, Andrew J. G.

Roberts, Patricia M.Roberts, Patricia M.

Smale, Terence C.Smale, Terence C.

Southgate, RobertSouthgate, Robert

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Article abstract of DOI:10.1039/P19810003242

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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Product name:4-{1-[Benzyloxycarbonyl-(triphenyl-λ5-phosphanylidene)-methyl]-4-oxo-azetidin-2-yl}-3-oxo-2-phenyl-butyric acid methyl ester

Cas No:81264-36-0

81264-36-0

R&D Labs maybe for 81264-36-0

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