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Synthetic Studies of the Tunicamycin Antibiotics. Preparation of (+)-Tunicaminyluracil, (+)-Tunicamycin-V, and 5'-epi-Tunicamycin-V

Myers, Andrew G. and Gin, David Y. and Rogers, Daniel H. (1994) Synthetic Studies of the Tunicamycin Antibiotics. Preparation of (+)-Tunicaminyluracil, (+)-Tunicamycin-V, and 5'-epi-Tunicamycin-V. Journal of the American Chemical Society, 116 (11). pp. 4697-4718. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20180601-150432322

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Abstract

A concise synthetic route to the tunicamycin antibiotics is described, illustrated by the preparation of (+)-tunicamycin-V (1-V), Key features of the synthesis include (1) the development and application of a silicon-mediated reductive coupling of aldehydes and allylic alcohols to construct the undecose core of the natural product and (2) the development of an efficient procedure for the synthesis of the trehalose glycosidic bond within the antibiotic. These innovations allow for the coupling of a uridine-derived aldehyde fragment with a performed trehalose-linked disaccharide allylic alcohol to form the carbohydrate core (1) of the natural product in a highly covergent manner. The resultant amino polyol is a versatile intermediate for the synthesis of any of the homologous tunicamycin antibiotics.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://dx.doi.org/10.1021/ja00090a018DOIArticle
Additional Information:© 1993 American Chemical Society. Received January 5, 1994. 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.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
ICI Americas Inc.UNSPECIFIED
GlaxoUNSPECIFIED
Natural Sciences and Engineering Research Council of Canada (NSERC)UNSPECIFIED
Other Numbering System:
Other Numbering System NameOther Numbering System ID
Arnold and Mabel Beckman Laboratories of Chemical Synthesis8905
Issue or Number:11
Record Number:CaltechAUTHORS:20180601-150432322
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180601-150432322
Official Citation:Synthetic Studies of the Tunicamycin Antibiotics. Preparation of (+)-Tunicaminyluracil, (+)-Tunicamycin-V, and 5'-epi-Tunicamycin-V Andrew G. Myers, David Y. Gin, and Daniel H. Rogers Journal of the American Chemical Society 1994 116 (11), 4697-4718 DOI: 10.1021/ja00090a018
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86756
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:01 Jun 2018 22:51
Last Modified:03 Oct 2019 19:47

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