sedamine and sedridine

sedamine has been researched along with sedridine* in 2 studies

Other Studies

2 other study(ies) available for sedamine and sedridine

ArticleYear
Synthesis of (+)-dumetorine and congeners by using flow chemistry technologies.
    Chemistry (Weinheim an der Bergstrasse, Germany), 2011, May-23, Volume: 17, Issue:22

    An efficient total synthesis of the natural alkaloid (+)-dumetorine by using flow technology is described. The process entailed five separate steps starting from the enantiopure (S)-2-(piperidin-2-yl)ethanol 4 with 29% overall yield. Most of the reactions were carried out by exploiting solvent superheating and by using packed columns of immobilized reagents or scavengers to minimize handling. New protocols for performing classical reactions under continuous flow are disclosed: the ring-closing metathesis reaction with a novel polyethylene glycol-supported Hoveyda catalyst and the unprecedented flow deprotection/Eschweiler-Clarke methylation sequence. The new protocols developed for the synthesis of (+)-dumetorine were applied to the synthesis of its simplified natural congeners (-)-sedamine and (+)-sedridine.

    Topics: Alkaloids; Catalysis; Cyclization; Molecular Structure; Piperidines; Solvents; Stereoisomerism; Technology; Temperature

2011
Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine.
    The Journal of organic chemistry, 2003, Nov-28, Volume: 68, Issue:24

    Kinetic resolution of N-Boc-piperidine-2-ethanol (2), a case of remote stereocenter discrimination, was accomplished by sequential transesterification mediated by two enzymes, Lipase PS and porcine pancreatic lipase, showing opposite enantioselectivity. The gram-scale availability of the two enantiomeric N-Boc alcohols 2a (R) and 2c (S) enlarges their synthetic exploitation for the enantioselective preparation of piperidine alkaloids. As an example, the convenient three-step synthesis of both the enantiomers of sedamine and allosedamine is described.

    Topics: Acetylation; Alkaloids; Animals; Kinetics; Lipase; Models, Chemical; Molecular Structure; Piperidines; Stereoisomerism

2003
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