title: Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor.
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.
authors.affiliation: Department of Organic and Inorganic Chemistry, NSRIM, University of Nijmegen, Toernooiveld, 6525 ED Nijmegen, The Netherlands.
authors.forename: Guuske F
authors.initials: GF
authors.lastname: Busscher
authors.forename: Stan
authors.initials: S
authors.lastname: Groothuys
authors.forename: René
authors.initials: R
authors.lastname: de Gelder
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
authors.forename: Floris L
authors.initials: FL
authors.lastname: van Delft