Tetrahedron

The synthesis of ester and ketone analogues of 1-deoxynojirimycin and castanospermine

…, G Joly, K Peeters, S Toppet, G Hoornaert, A Kilonda

Index: Compernolle, Frans; Joly, Gert; Peeters, Koen; Toppet, Suzanne; Hoornaert, Georges; Kilonda, Amuri; Babady-Bila Tetrahedron, 1997 , vol. 53, # 37 p. 12739 - 12754

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Citation Number: 21

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- ...