Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor.
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SourceJournal of Organic Chemistry, 69, 13, (2004), pp. 4477-4481
Article / Letter to editor
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Synthetic Organic Chemistry
Solid State Chemistry
Journal of Organic Chemistry
SubjectMolecular Materials; Synthetic Organic Chemistry
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.
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