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Synthesis of the Thiazolone Analogue of the Acetylcholinesterase Inhibitor, Huperzine A

✍ Scribed by Alan P. Kozikowski; Werner Tückmantel; Ashima Saxena; Bhupendra P. Doctor

Book ID
102858640
Publisher
John Wiley and Sons
Year
1994
Tongue
German
Weight
792 KB
Volume
77
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 (→ 8; Scheme 1) and then constructing the bicyclo[3.3.1]nonane substructure using our previously described Michael addition/aldol condensation methodology (Scheme 3). The central problem was the protection of the thiazolone carbonyl group; only the 2‐unsubstituted thiazole survived the reaction conditions of the first half of the synthesis. Refunctionalization was later effected by lithiation and subsequent chlorination with hexachloroethane (30→31). Compound 3a was ineffective in the acetylcholinesterase inhibition assay in concentrations up to 14 μM.

📜 SIMILAR VOLUMES

ChemInform Abstract: Synthesis of a Hybr
ChemInform Abstract: Synthesis of a Hybrid Analogue (I) of the Acetylcholinesterase Inhibitors Huperzine A and Huperzine B.
✍ V. Rajendran; Suo-Bao Rong; Ashima Saxena; Bhupendra P. Doctor; Alan P. Kozikows 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 26 KB 👁 2 views

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