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
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Singh, Priyanka
Manna, S K Panda, Gautam |
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| Date |
2014-05-13T09:13:04Z
2014-05-13T09:13:04Z 2014 |
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| Identifier |
Tetrahedron 2014,70,1363-1374
http://hdl.handle.net/123456789/1236 |
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| 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
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316462 bytes
application/pdf |
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| Language |
en
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| Relation |
CSIR-CDRI communication no.8570
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| Subject |
Synthesis
Polyhydroxylated Piperidines Pentahydroxy Indolizidines Diversity |
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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
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Article
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