Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes
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nihms-1042299.pdf
Description
Accepted version
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821.59 KB
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c71e5a748ecf14d49375170bb5c4a738
Author(s)
McGeough, Catherine P.
Strom, Alexandra E.
Jamison, Timothy F
Date Issued
May 2019
Journal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
McGeough, Catherine P. et al., "Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes." Organic Letters 21, 10 (May 2019): p. 3606–09 doi. 10.1021/acs.orglett.9b01019 ©2019 Authors
Version
Author's final manuscript
Abstract
Skipped polyenes featuring high (E)-selectivity and varying methyl substitution patterns are synthesized using a nickel-catalyzed cross-coupling reaction between allyl trifluoroacetates and vinyl bromides. The utility of this cross-electrophile coupling is showcased in part by the synthesis of the RST fragment of the marine ladder polyether, maitotoxin. Construction of this fragment is particularly challenging due to the alternating methyl substitution pattern. ©2019 American Chemical Society.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ACS.ORGLETT.9B01019
