Natural products as templates for bioactive compound libraries: Part 2. Novel modifications of vasicine (peganine) core via efficient and regioselective generation of 3-lithiodeoxyvasicine and its stereoselective addition to aliphatic ketones§

Author： Shevyakov Sergey V.

Publisher： Taylor & Francis Ltd

ISSN： 1478-6419

Source： Natural Product Research, Vol.20, Iss.9, 2006-07, pp. : 871-881

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Abstract

A general procedure for direct lithiation of deoxyvasicine was developed. 3-Lithiodeoxyvasicine intermediate was found to react with various aliphatic ketones providing derivatives of 3-(hydroxyalkyl)deoxyvasicine in good yields. Similar reaction with 4-alkylcyclohexanones yielded respective trans -adducts exclusively. This novel protocol was successfully scaled-up to result in multigram quantities of vasicine-containing core building blocks suitable for production of compound libraries. The described synthetic methodology offers access to a wide range of compounds with potentially beneficial biological profiles.