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

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.

SUBMITTER: McGeough CP 

PROVIDER: S-EPMC6681449 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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

McGeough Catherine P CP   Strom Alexandra E AE   Jamison Timothy F TF  

Organic letters 20190502 10

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. ...[more]

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