Miscellaneous Functionalized Derivatives of 3-Amino-3-Deoxyhexoses of Antibiotics and Their Conversion into Other Organic Substances

Abstract

The numerous synthetic routes worked out during the past twenty years for the production of 3-amino-2,3,6-trideoxyhexoses offered the challenge of further derivatization of these sugars and the intermediates in their syntheses. Such research was apparently stimulated and promoted by the goal of discovering semisynthetic anthracycline antibiotics that exhibit the same or higher antitumor activity along with diminished toxic side effects, thereby extending the limited therapeutic utility of the parent antibiotics. In addition, based on analogies taken from other fields of biologically active carbohydrate substances, structurally related derivatives containing a daunosamine-type aminodeoxy hexose moiety have also been prepared. The widening interest and research on the utilization of the derivatives of such aminosugars as “chiral templates” (561) in natural products syntheses apparently demonstrate the importance of this group of highly functionalized carbohydrates both chemically and biologically.