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