Towards the total synthesis of keramaphidin B

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Abstract

The enantio- and diastereoselective Michael addition of a δ-valerolactone-derived pronucleophile to a substituted furanyl nitroolefin catalysed by a bifunctional cinchonine-derived thiourea has been used as the key stereocontrolling step in a new synthetic strategy to the heavily functionalised piperidine core of keramaphidin B.

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Jakubec, P., Farley, A. J. M., & Dixon, D. J. (2016). Towards the total synthesis of keramaphidin B. Beilstein Journal of Organic Chemistry, 12, 1096–1100. https://doi.org/10.3762/bjoc.12.104

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