[2,3]-Wittig rearrangement approach to iminosugar C-glycosides: 5-epi-ethylfagomine, 2-epi-5-deoxyadenophorine and formal synthesis of indolizidine 167B and 209D |
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| Authors: | B ChandrasekharJ Prasada Rao B Venkateswara Rao P Naresh |
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| Institution: | a Organic Division III, Indian Institute of Chemical Technology, Hyderabad, India
b Centre for Nuclear Magnetic Resonance, Indian Institute of Chemical Technology, Hyderabad, India |
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| 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. |
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