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Title: Synthesis of polyhydroxylated indolizidines and piperidines from Garner’s aldehyde: Total synthesis of (-)-Swainsonine, (+)-1,2-Di-epi-swainsonine, (+)-8,8a-Di-epi-castanospermine, Pentahydroxy Indolizidines, (-)-1-Deoxynojirimycin, (-)-1-Deoxy-altro-nojirimycin and related diversity
Authors: Singh, Priyanka;Manna, S K;Panda, Gautam
subject: Synthesis;Polyhydroxylated;Piperidines;Pentahydroxy Indolizidines;Diversity
Year: 2014
Description: Diastereoselective and diverse synthesis of polyhydroxylated indolizidines and piperidines have been described, where a common chiral intermediate 2-(hydroxymethyl) piperidine-3-ol is converted into (-)-Swainsonine, (+)-1,2-Di-epi-swainsonine, (+)-8,8a-Di-epi-castanospermine, Pentahydroxy Indolizidines, (-)-1-Deoxynojirimycin, (-)-1-Deoxy-altro-nojirimycin and related diversity. The key steps were hydroxy directed intramolecular aminomercuration, Mitsunobu cyclisation and diastereoselective dihydroxylation. © 2014 Elsevier Science. All rights reserved
Standard no: Tetrahedron 2014,70,1363-1374
Appears in Collections:Medicinal and Process Chemistry

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