A Chiral Synthesis of (+)-Pseudoconhydrine

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Abstract
(+)-Pseudoconhydrine, 1 of the hemlock alkaloids, was synthesized from methyl 2-acetamido-2,3,4-trideoxy-.alpha.-D-erythro-hexopyranoside by an 11 step reaction sequence. An intra-molecular nucleophilic attack of the nitrogen atom on 2-acetamido-5-O-benzyl-2,3-4-trideoxy-6-O-tosyl-D-erythro-hexose diethyl dithioacetal to the terminal tosyloxymethylene group proceeded smoothly and gave the desired disubstituted piperidine compound. A conversion of the thioacetal group into an aldehyde, a 2-carbon elongation by Wittig olefination, and a successive hydrogenation completed the chiral synthesis of the title alkaloid.