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| Title: | Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor |
| Author(s): | Busscher, G.F.
Groothuys, S. (29898072X)
Gelder, R. de (100727905)
Rutjes, F.P.J.T. (107543486)
Delft, F.L. van (148050832) |
| Publication year: | 2004 |
| Document type: | Article / Letter to editor |
| Journal: | Journal of organic chemistry |
| ISSN: | 0022-3263 |
| Volume: | vol. 69 |
| Issue: | iss. 13 |
| Start page: | p. 4477 |
| End page: | p. 4481 |
| Abstract: | A synthesis route toward 2-deoxystreptamine, a common structure in many of the clinically important aminoglycosides, is presented. Starting from p-benzoquinone and cyclopentadiene, 2-deoxystreptamine is synthesized with key steps involving Pd(0)-catalyzed rearrangement, a retro-Diels-Alder by flash vacuum thermolysis, and Yb(III)-directed regioselective epoxide opening. The obtained diazidocyclitol 17 is a suitable 2-deoxystreptamine precursor, conveniently protected for incorporation in new aminoglycoside entities. |
| Subject: | Molecular Materials
Synthetic Organic Chemistry |
| Organization: | Synthetic Organic Chemistry
Molecular Materials |
| Appears in Collections: | Academic bibliography
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Please use this identifier to cite or link to this item:
http://hdl.handle.net/2066/58592
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