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A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core

Cowper, Nicholas G. W. and Hesse, Matthew J. and Chan, Katie M. and Reisman, Sarah E. (2020) A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core. Chemical Science, 11 (43). pp. 11897-11901. ISSN 2041-6520. https://resolver.caltech.edu/CaltechAUTHORS:20201015-152733817

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Abstract

The bicyclic tetrahydro-1,2-oxazine subunit of gliovirin is synthesized through a diastereoselective copper-catalyzed cyclization of an N-hydroxyamino ester. Oxidative elaboration to the fully functionalized bicycle was achieved through a series of mild transformations. Central to this approach was the development of the first catalytic, enantioselective propargylation of an oxime to furnish a key N-hydroyxamino ester intermediate.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1039/d0sc04802jDOIArticle
ORCID:
AuthorORCID
Cowper, Nicholas G. W.0000-0003-4857-6052
Hesse, Matthew J.0000-0002-4759-5086
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© The Author(s) 2020. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Received 1st September 2020. Accepted 3rd October 2020. First published 15 Oct 2020. All publication charges for this article have been paid for by the Royal Society of Chemistry. We gratefully acknowledge Dr Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, Dr David VanderVelde for assistance with NMR structure analysis, and Dr Michael K. Takase for X-ray crystallographic structure determination. We thank Materia, Inc. for donations of metathesis catalysts. S. E. R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (R35GM118191-01) is gratefully acknowledged. There are no conflicts to declare.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
Heritage Medical Research InstituteUNSPECIFIED
NIHR35GM118191-01
Royal Society of ChemistryUNSPECIFIED
Issue or Number:43
Record Number:CaltechAUTHORS:20201015-152733817
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20201015-152733817
Official Citation:A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core. Chem. Sci., 2020, 11, 11897-11901; doi: 10.1039/d0sc04802j
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:106097
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:16 Oct 2020 16:33
Last Modified:11 Nov 2020 19:08

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