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A convergent synthetic route to the tunicamycin antibiotics. Synthesis of (+)-tunicamycin V

Abstract

The tunicamycins are a family of natural products represented generally by structure 1, wherein R indicates one of several long-chain branched, linear, saturated or unsaturated acyl substituents. They elicit a considerable range of biological responses including antimicrobial, antifungal, antiviral, and antitumor activities. Their ability to function as potent inhibitors of oligosaccharide synthesis in eukaryotic cells has established them as unique biochemical probes of the role of glycosylation on protein structure and function. In this work, we describe a concise synthetic route to the tunicamycins, illustrated by the preparation of (+)-tunicamycin V (1-V)

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