Synthesis of the thiazolone analogue of the acetylcholinesterase inhibitor, huperzine A

AP Kozikowski, W Tückmantel, A Saxena…

Index: Kozikowski; Tuckmantel; Saxena; Doctor Helvetica Chimica Acta, 1994 , vol. 77, # 5 p. 1256 - 1266

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Citation Number: 25

Abstract

Abstract The preparation of an analogue 3a of the acetylcholinesterase inhibitor, huperzine A (1), is described in which the pyridinone moiety of the natural product is replaced with a thiazolone moiety. The synthesis started from cyclohexane-1, 4-dione monoethylene ketal (7) by first annulating the thiazole ring using the Gewald protocol ([RIGHTWARDS ARROW] 8; Scheme 1) and then constructing the bicyclo [3.3. 1] nonane substructure using our ...