Published December 15, 2020
| Version v1
Journal article
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Total Syntheses of Paraconic Acids and 1,10-seco-Guaianolides via Barbier Allylation/Translactonization Cascade of 3-(Bromomethyl)-2(5H)-furanone
Creators
- 1. Department of Organic Chemistry, NCCR Chemical Biology, Faculty of Science, University of Geneva, 1205 Geneva, Switzerland.
Description
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 umpolung of π-allylpalladium as a nucleophile and promoting a Lewis acid mediated translactonization. This sequence showed 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.
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