Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor.
Publication year
2004Source
Journal of Organic Chemistry, 69, 13, (2004), pp. 4477-81ISSN
Publication type
Article / Letter to editor
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Organization
Synthetic Organic Chemistry
Solid State Chemistry
Journal title
Journal of Organic Chemistry
Volume
vol. 69
Issue
iss. 13
Page start
p. 4477
Page end
p. 81
Subject
Molecular Materials; Synthetic Organic ChemistryAbstract
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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