Dhavale, Dilip D. ; Jachak, Santosh M. ; Karche, Navnath P. ; Trombini, Claudio (2004) Synthesis of trihydroxy quinolizidine alkaloids: 1,3-addition reaction of allylmagnesium bromide to a sugar nitrone Tetrahedron, 60 (13). pp. 3009-3016. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/j.tet.2004.01.085
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Azasugar; Carbohydrate; Quinolizidine; Glycosidase; Inhibitor |
| ID Code: | 9735 |
| Deposited On: | 02 Nov 2010 10:47 |
| Last Modified: | 31 May 2011 11:56 |
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