Publication 11 of year 2021

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  1. Total Syntheses of Paraconic Acids and 1,10-seco -Guaianolides via a Barbier Allylation/Translactonization Cascade of 3-(Bromomethyl)-2(5H )-furanone
    Liu, W.; Yu, Z.; Winssinger, N.
    Org. Lett. 2021, 23, 969-973

A palladium-catalyzed Barbier allylation/translactonization cascade reaction was established for the rapid construction of β,γ-disubstituted α-exo-methylene-γ-butyrolactone, an important motif in sesquiterpenes. Dimethyl zinc played significant roles in both steps for the umpolung of π-allylpalladium as a nucleophile and promoting a Lewis acid-mediated translactonization. This sequence showed a broad substrate scope and was further harnessed for the synthesis of two paraconic acids as well as the first protecting-group-free total synthesis of two 1,10-seco-guaianolides.

DOI: 10.1021/acs.orglett.0c04165 

open archive unige:148589