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Stereoselective Route towards 2,5-Disubstituted Piperidine Alkaloids. Synthesis of (+)-Pseudoconhydrine and (±)-epi-Pseudoconhydrine

✍ Scribed by Joakim Löfstedt; Helena Pettersson-Fasth; Jan-E Bäckvall

Book ID
104209849
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
144 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐThis 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-de®ned anti and syn aminoalcohol derivatives, 1-benzyloxy-5-(p-toluenesulfonamido)-3-alken-2-ols (5), which were transformed to (1)pseudoconhydrine ( 3) and (^)-epi-pseudoconhydrine (9), respectively, via protection (silyl ether), hydrogenation, debenzylation and cyclization. Detosylation±deprotection gave the ®nal products in good yields and high stereoisomeric purity.

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