Synthesis of trihydroxy quinolizidine alkaloids: 1,3-addition reaction of allylmagnesium bromide to a sugar nitrone |
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Authors: | Dilip D Dhavale Santosh M Jachak Claudio Trombini |
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Institution: | a Department of Chemistry, Garware Research Centre, University of Pune, Pune 411 007, India b Dipartimento di Chimica “G. Ciamician”, via Selmi-2, 40126 Bologna, Italy |
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Abstract: | The synthesis of (1R,2R,3S,9aR) and (1R,2R,3S,9aS) trihydroxy quinolizidine alkaloids 3a and 3b from d-glucose derived nitrone 4 is described. The key transformation involves the 1,3-addition of allylmagnesium bromide to nitrone 4 that afforded high diastereoselectivity in the presence of TMSOTf. The N-O bond reductive cleavage, N-Cbz protection, ozonolysis, Wittig olefination, lactum formation and reductive amination cascade afforded the target compounds 3a and 3b in good overall yield. |
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Keywords: | Nitrone Azasugar Carbohydrate Quinolizidine Glycosidase Inhibitor |
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