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Published March 10, 1993 | Supplemental Material
Journal Article Open

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).

Additional Information

© 1993 American Chemical Society. Received November 23, 1992. This research was generously supported by the National Science Foundation, ICI Americas Inc., and Glaxo Inc. D.Y.G. acknowledges a doctoral fellowship from the Natural Sciences and Engineering Research Council of Canada.

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Supplemental Material - ja00058a060_si_001.pdf

Supplemental Material - ja2036.pdf

Supplemental Material - ja2036a.pdf

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