Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes

Authors

Catherine P. McGeough, Massachusetts Institute of Technology
Alexandra E. Strom, Stanford UniversityFollow
Timothy F. Jamison, Massachusetts Institute of Technology

Document Type

Article

Publication Date

5-17-2019

Publication Title

Organic Letters

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.

Volume

21

Issue

10

First Page

3606

Last Page

3609

DOI

10.1021/acs.orglett.9b01019

ISSN

15237060

Comments

Peer reviewed accepted manuscript.

Recommended Citation

McGeough, Catherine P.; Strom, Alexandra E.; and Jamison, Timothy F., "Ni-Catalyzed Cross-Electrophile Coupling for the Synthesis of Skipped Polyenes" (2019). Chemistry: Faculty Publications, Smith College, Northampton, MA.
https://scholarworks.smith.edu/chm_facpubs/79