synthesis of enantiomerically pure all cis-2,3,6-trisubstituted piperidine: a silicon mediated total...

2002 Alkaloids Alkaloids U 0600 Synthesis of Enantiomerically Pure all cis-2,3,6-Trisubstituted Piperidine: A Sili- con Mediated Total Synthesis of (+)-Carpamic Acid. — The stereoselective total synthesis of (+)-carpamic acid (XI) is based on the asymmetric desymmetrization of the glutaric anhydride (I) using the oxazolidinone (II), the diastereoselective α-methy- lation of the ester (VI) and a highly diastereoselective hyrogenation of an imine, gen- erated in situ by cyclization of the deprotected Cbz-amine (IX). — (SINGH, R.; GHOSH*, S. K.; Tetrahedron Lett. 43 (2002) 43, 7711-7715; Bio-Org. Div., Bhabha At. Res. Cent., Trombay, Bombay 400 085, India; Eng.) — Mais 02- 188

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Page 1: Synthesis of Enantiomerically Pure all cis-2,3,6-Trisubstituted Piperidine: A Silicon Mediated Total Synthesis of (+)-Carpamic Acid

2002 Alkaloids

AlkaloidsU 0600 Synthesis of Enantiomerically Pure all cis-2,3,6-Trisubstituted Piperidine: A Sili-

con Mediated Total Synthesis of (+)-Carpamic Acid. — The stereoselective total synthesis of (+)-carpamic acid (XI) is based on the asymmetric desymmetrization of the glutaric anhydride (I) using the oxazolidinone (II), the diastereoselective α-methy-lation of the ester (VI) and a highly diastereoselective hyrogenation of an imine, gen-erated in situ by cyclization of the deprotected Cbz-amine (IX). — (SINGH, R.; GHOSH*, S. K.; Tetrahedron Lett. 43 (2002) 43, 7711-7715; Bio-Org. Div.,Bhabha At. Res. Cent., Trombay, Bombay 400 085, India; Eng.) — Mais

02- 188

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