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Towards the total synthesis of keramaphidin B
Pavol Jakubec1, Alistair J M Farley1, Darren J Dixon1
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom.
Beilstein Journal of Organic Chemistry
|June 25, 2016
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.
Keywords:
bifunctional organocatalystenantioselective Michael additionkeramaphidin Bnitro-Mannich lactamisation cascade
