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

Weilong Liu | Zendy; Zhimei Yu | Zendy; Nicolas Winssinger | Zendy

Open Access

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

Author(s) -

Weilong Liu,

Zhimei Yu,

Nicolas Winssinger

Publication year - 2021

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c04165

Subject(s) - chemistry , umpolung , lewis acids and bases , methylene , nucleophile , stereochemistry , palladium , organic chemistry , catalysis

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.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research