81418-01-1Relevant articles and documents
Microwave-assisted telescoped cross metathesis-ring closing aza-Michael reaction sequence: step-economical access to nicotine-lobeline hybrid analogues
Drège,Oko,Venot,Gigant,Joseph
, p. 96720 - 96724 (2015)
A series of 2,5-disubstituted pyrrolidines was synthesized through an efficient telescoped cross-metathesis/cyclizing aza-Michael addition involving N-heteroaromatic olefinic derivatives. This synthetic route was applied to the preparation of original nicotine-lobeline, nicotine-pelletierine and lobeline-nicotine-epibatidine hybrids.
Design, synthesis and decoration of molecular scaffolds for exploitation in the production of alkaloid-like libraries
Craven, Philip,Aimon, Anthony,Dow, Mark,Fleury-Bregeot, Nicolas,Guilleux, Rachel,Morgentin, Remy,Roche, Didier,Kalliokoski, Tuomo,Foster, Richard,Marsden, Stephen P.,Nelson, Adam
supporting information, p. 2629 - 2635 (2015/01/30)
The design, synthesis and decoration of six small molecule libraries is described. Each library was inspired by structures embedded in the framework of specific alkaloid natural products. The development of optimised syntheses of the required molecular scaffolds is described, in which reactions including Pd-catalysed aminoarylation and diplolar cycloadditions have been exploited as key steps. The synthesis of selected exemplar screening compounds is also described. In five cases, libraries were subsequently nominated for production on the basis of the scope and limitations of the validation work, as well as predicted molecular properties. In total, the research has led to the successful synthesis of >2500 novel alkaloid-like compounds for addition to the screening collection (the Joint European Compound Library, JECL) of the European Lead Factory.
Directed intermolecular carbomagnesation across vinylsilanes: 2-PyMe2Si group as a removable directing group
Itami, Kenichiro,Mitsudo, Koichi,Yoshida, Jun-Ichi
, p. 2337 - 2339 (2007/10/03)
Facile addition of primary alkyl Gridnard reagents to vinylsilanes has been realized for the first time by exploiting the directing effect of a 2-pridyl group on silicon [Eq. (1)]. Three-component coupling reactions of a Grignard reagent, the vinylsilane,