F. Compernolle, G. Joly, K. Peeters
Sep 15, 1997
Citations
0
Influential Citations
11
Citations
Journal
Tetrahedron
Abstract
Abstract 1-Amino-1-deoxy-D-glucitol (3) was converted into the 3,4;5,6-di-O-isopropylidene protected ammonium salt 17 which was transformed further into the trans-fused piperidine acetonides 4–8 in six steps and 23–32% overall yield. In the final step, ring closure was effected via cleavage of the N-Boc group of intermediates 27–29 with trimethylsilyl iodide: this enabled internal, face selective 1,4-addition of the free amino group to the (5,6)-α,β-unsaturated carbonyl moiety. Further modification and (or) deprotection of compounds 4–8 afforded the piperidine and indolizidine imino sugars 9–12 and 14–15.