[2,3]-Wittig rearrangement approach to iminosugar C-glycosides: 5-epi-ethylfagomine, 2-epi-5-deoxyadenophorine and formal synthesis of indolizidine 167B and 209D

Authors :: Chandrasekhar, B.
Prasada Rao, J.
Venkateswara Rao, B.
Naresh, P.
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Nov2011, Vol. 52 Issue 45, p5921-5925. 5p.
Publication Year :: 2011
Abstract: Abstract: A new strategy for the synthesis of 1,2-dideoxy iminosugar C-glycosides and indolizidines involving highly stereoselective [2,3]-Wittig rearrangement from Garner aldehyde has been developed. This rearrangement yielded an optically pure, highly functionalized key intermediate, which has been further utilized for the synthesis of 5-epi-ethylfagomine, 2-epi-5-deoxyadenophorine, and 5-hydroxymethyl indolizidine. [Copyright &y& Elsevier]

Subjects :: *ORGANIC synthesis
*REARRANGEMENTS (Chemistry)
*IMINOSUGARS
*GLYCOSIDES
*GLUCOSAMINE
*INDOLE
*ALDEHYDES

Language :: English
ISSN :: 00404039
Volume :: 52
Issue :: 45
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 66398674
Full Text :: https://doi.org/10.1016/j.tetlet.2011.08.084

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