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Literature DB >> 31046296

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

Catherine P McGeough¹, Alexandra E Strom¹, Timothy F Jamison¹.

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.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2019 PMID： 31046296 PMCID： PMC6681449 DOI： 10.1021/acs.orglett.9b01019

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

23 in total

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Authors: Ivan Vilotijevic; Timothy F Jamison
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5. Water overcomes methyl group directing effects in epoxide-opening cascades.

Authors: Christopher J Morten; Timothy F Jamison
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6. Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions using allylindium generated in situ from allyl acetates, indium, and indium trichloride.

Authors: Dong Seomoon; Kooyeon Lee; Hyunseok Kim; Phil Ho Lee
Journal: Chemistry Date: 2007 Impact factor: 5.236

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

1. Total synthesis of (-)-hennoxazole A.

2. Structure assignment of lagunapyrone B by fluorous mixture synthesis of four candidate stereoisomers.

3. Endo-oxacyclizations of polyepoxides: biomimetic synthesis of fused polycyclic ethers.

4. Epoxide-opening cascades promoted by water.

5. Water overcomes methyl group directing effects in epoxide-opening cascades.

6. Inter- and intramolecular palladium-catalyzed allyl cross-coupling reactions using allylindium generated in situ from allyl acetates, indium, and indium trichloride.

7. New chemical cross-coupling between aryl halides and allylic acetates using a cobalt catalyst.

8. Iromycins from Streptomyces sp. and from synthesis: new inhibitors of the mitochondrial electron transport chain.

9. Alkene substituents for selective activation of endo-regioselective polyepoxide oxacyclizations.

10. Selective disruption of the E-cadherin-catenin system by an algal toxin.

1. Synthesis of the EFG Framework of Tamulamides A and B.