Rhodium-Catalyzed Endo -Selective Epoxide-Opening Cascades: Formal Synthesis of (−)-Brevisin
Name
Jamison_Rhodium-Catalyzed.pdf
Size
440.51 KB
Format
Adobe PDF
Checksum (MD5)
6551556273da9fcd599e39e07ef9de75
Author(s)
Armbrust, Kurt
Beaver, Matthew G.
Jamison, Timothy F
Date Issued
June 2015
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Armbrust, Kurt W.; Beaver, Matthew G. and Jamison, Timothy F. “ Rhodium-Catalyzed Endo -Selective Epoxide-Opening Cascades: Formal Synthesis of (−)-Brevisin.” Journal of the American Chemical Society 137, 21 (June 2015): 6941–6946 © 2015 American Chemical Society
Version
Author's final manuscript
Abstract
[Rh(CO)₂Cl]₂ is as an effective catalyst for endo-selective cyclizations and cascades of epoxy-(E)-enoate alcohols, thus enabling the synthesis of oxepanes and oxepane-containing polyethers from di- and trisubstituted epoxides. Syntheses of the ABC and EF ring systems of (−)-brevisin via all endo-diepoxide-opening cascades using this method constitute a formal total synthesis and demonstrate the utility of this methodology in the context of the synthesis of marine ladder polyether natural products.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-Noncommercial-Share Alike
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/jacs.5b03570
