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Synthetic approaches to racemic porantheridine and 8-epihalosaline via a nitroso Diels-Alder cycloaddition/ring-rearrangement metathesis sequence.
- Pierre Sancibrao, D. Karila, C. Kouklovsky, G. Vincent
- Chemistry, BiologyThe Journal of organic chemistry
- 26 May 2010
The formation of the 2,6-trans-disubstituted piperidine backbone of porantheridine has been accomplished by addition of a Grignard reagent onto an N-benzylpiperidone followed by a highly diastereoselective reduction of the imminium intermediate in one pot.
Stereodivergent synthesis of piperidine alkaloids by ring-rearrangement metathesis/reductive lactam alkylation of nitroso Diels-Alder cycloadducts.
- G. Vincent, D. Karila, G. Khalil, Pierre Sancibrao, D. Gori, C. Kouklovsky
- 8 July 2013
A general methodology for the stereoselective synthesis of 2-(2-hydroxyalkyl)piperidine alkaloids by ring-rearrangement metathesis of nitroso Diels-Alder cycloadducts is reported. The approach is…
Synthesis of oxaspirannic building blocks by regioselective nitroso-Diels-Alder reactions.
Spirocyclic structures: Nitroso-Diels-Alder reactions of 1,3-disubstituted cyclohexadienes were found to be regiodivergent, depending on the nitroso derivative used. Cycloaddition with Wightman's…