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2005
Pyridine derivatives
R 0380
A General Approach to (5S,6R)-6-Alkyl-5-benzyloxy-2-piperidinones: Applicato the Asymmetric Syntheses of Neurokinin Substance P Receptor Antagonist
01- 121 tion
(-)-L-733,061 and (-)-Deoxocassine. — The piperidinediones (I) and (X) are found to
react with Grignard compounds with high regio- and stereoselectivity (86-97% regioselectivity). Subsequent reductive deoxygenation predominantly yields trans-5,6-disubstituted 2-piperidinones like (V), (VIII), and (XI). The latter are potent synthetic
synthons which can be transformed into (-)-L-733,061 (IX), (-)-deoxocassine (VI), and
the HIV protease inhibitor (XII). — (LIU, L.-X.; RUAN, Y.-P.; GUO, Z.-Q.;
HUANG*, P.-Q.; J. Org. Chem. 69 (2004) 18, 6001-6009; Dep. Chem., Xiamen
Univ., Xiamen 361005, Fujian, Peop. Rep. China; Eng.) — Jannicke
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