Published November 21, 2020
| Supplemental Material + Published
Journal Article
Open
A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core
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.
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.Attached Files
Published - d0sc04802j.pdf
Supplemental Material - d0sc04802j1.pdf
Supplemental Material - d0sc04802j2.cif
Files
d0sc04802j.pdf
Additional details
- PMCID
- PMC8162951
- Eprint ID
- 106097
- Resolver ID
- CaltechAUTHORS:20201015-152733817
- Heritage Medical Research Institute
- R35GM118191-01
- NIH
- Royal Society of Chemistry
- Created
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2020-10-16Created from EPrint's datestamp field
- Updated
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2021-06-07Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute