Total Syntheses of Paraconic Acids and 1,10-seco-Guaianolides via a Barbier Allylation/Translactonization Cascade of 3-(Bromomethyl)-2(5H)-furanone

Article Article scientifique Article Total Syntheses of Paraconic Acids and 1,10-seco-Guaianolides via a Barbier Allylation/Translactonization Cascade of 3-(Bromomethyl)-2(5H)-furanone eng 2021 author Liu Weilong 882504 author Yu Zhimei 936063 author Winssinger Nicolas 769664 969-973 10.1021/acs.orglett.0c04165 1523-7052 https://pubs.acs.org/doi/10.1021/acs.orglett.0c04165 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. Dewey 540 36 Département de chimie organique 141 false 762 Groupe Winssinger Organic Letters 23 3 1e91a96a-ec93-4c83-8167-787bd39984ba Article (Published version) Restricted acs.orglett.0c04165.pdf 1221512 application/pdf cacbd159-7a43-44ed-afc8-00aaf9df261c Article (Accepted version) Public 148589-TotalSynthesis Paraconic aci.pdf 4460775 application/pdf 62eeb13798baa891a09b808291ec14e8583d522d902bebff3bcd537fea103c86 openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Total Syntheses of Paraconic Acids and 1,10-seco-Guaianolides via a Barbier Allylation/Translactonization Cascade of 3-(Bromomethyl)-2(5H)-furanone	Organic Letters			2021	549	208

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Yu, Zhimei