Formal synthesis of L-altro-1-deoxynojirimycin, cis-3-hydroxypipecolic acid along with synthesis of (R)-piperidinol and a conceptually different advanced intermediate for non-natural piperidine alkaloids is reported from cis-butene-1,4-diol. The key reactions involved are Johnson–Claisen rearrangement, Sharpless asymmetric dihydroxylation, reductive lactamization and novel regioselective elimination.
S. P. Chavan, N. B. Dumare and K. P. Pawar, RSC Adv., 2014, 4, 32594 DOI: 10.1039/C4RA04558K
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