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 stereodefined anti 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.
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