TETRAHEDRON LETTERS

Abstract—3,4-Diamino-3,4-dideoxy-L-chiro-inositol has been prepared from bromobenzene by a chemoenzymatic approach. The key chemical step was a tetrabutylammonium fluoride (TBAF) catalyzed vinyl aziridine opening employing p-toluenesulfonamide as a nucleophile, establishing the 1,2-trans relationship of the amino groups. © 2001 Elsevier Science Ltd. All rights reserved. Unnatural inositol derivatives with amino groups sub-stituted for one or more hydroxyl groups have attracted interest as probes for the investigation of the inositol-phosphate cycle as well as potential glycosidase inhibitors, and several diaminocyclitol aminoglycosides possess antibiotic activities. The aminocyclitol unit in the great majority of these aminoglycoside antibiotics is either 2-deoxystreptamine (1) or streptamine (2),1 both featuring a 1,3-arrangement of the two amino groups (Fig. 1). Several syntheses of streptamine derivatives containing either a 1,3-2,3 or a 1,4 relationship4 of the nitroge