A 3-step synthesis of the biologically active metabolites (2 and 3) of imidacloprid from aminoacetaldehyde diethyl acetal or ethylenediamine was developed. A series of new imidacloprid analogues were also prepared.
~~~~~~~The title compounds 2 and their corresponding (6 S ) epimers 18 are prepared in several steps by starting with chiral formyl ester 5, and a-tetralones 10: (1) coupling reaction with the ylide generated from 11 to yield unsaturated ester 13, (2) reduction to the corresponding alcohol 14, (3) addition of the Grignard reagent derived from 14 to formyl ester 5 to afford the hydroxy esters 16 and 17, and (4) lactonization. This procedure is also used to synthesize the p-naphthyl analogs 29 and 30. Some results obtained from HMG-CoA reductase inhibitor screening are also reported.
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