Stereoselective route towards 2,5-disubstituted ...



Title Stereoselective route towards 2,5-disubstituted piperidine alkaloids. Synthesis of (+)-pseudoconhydrine and (±)-epi-pseudoconhydrine
Author(s) Jeanne Lofstedt, H. Pettersson-Fasth, J. E. Backvall
Journal Tetrahedron
Date 2000
Volume 56
Issue 15
Start page 2225
End page 2230
Abstract This paper describes a new general approach towards functionalized piperidine alkaloids, based on the stereo- and regioselective palladium(0)-catalyzed nucleophilic ring-opening of vinyl epoxides by nitrogen nucleophiles. The latter reaction provides access to stereo-defined and and syn aminoalcohol derivatives, 1-benzyloxy-5-(p-toluenesulfonamido)-3-alken-2-ols (5), which were transformed to (+)-pseudoconhydrine (3) and (+/-)-epi-pseudoconhydrine (9), respectively, via protection (silyl ether), hydrogenation, debenzylation and cyclization. Detosylation-deprotection gave the final products in good yields and high stereoisomeric purity. (C) 2000 Elsevier Science Ltd. All rights reserved.

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