New synthetic methodology en route to asymmetric piperidine alkaloids

Piperidine synthesis - Organic chemistry

The Yu Lab - The Scripps Research Institute

Asymmetric synthesis of pharmacologically interesting piperidine-fused spiro-oxindole derivatives has been achieved via an organocatalytic Michael/aza-Henry/hemiaminalization cascade reaction. Chiral compounds synthesized by this strategy potently inhibited the proliferation of several breast cancer cell lines. Mechanistic studies suggest that the most potent compound 9e can directly interfere with MDM2–p53 interactions and elevate protein levels of p53 and p21, thereby inducing cell cycle arrest and mitochondrial apoptosis.

Article: Synthesis of Enantioenriched 2 Alkyl Piperidine Derivatives through Asymmetric Reduction of Pyridinium Salts. Advertisement

Journal of Coordination Chemistry: Vol 70, No 22

Using DTR, a variety of electrophiles can be used to provide an asymmetric synthesis of enantiomerically enriched 2-substituted piperidines, including (after Boc deprotection) the alkaloid (+)-β-conhydrine.

α-Amino 1,3-Dithioketal Mediated Asymmetric Synthesis of Piperidines (L-733,060) and Tetrahydrofuran Glycines

Sulfinimine-derived α-amino 1,3-dithianes, α-amino carbonyl chiral building blocks, are utilized in asymmetric syntheses of (+)-(tetrahydrofuran-2-yl)glycine and the 2,3-disubstituted piperidine (+)-L-733,060.

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