Journal
ORGANIC LETTERS
Volume 23, Issue 3, Pages 969-973Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c04165
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Funding
- Swiss National Science Foundation [200020_188406]
- Swiss National Science Foundation (SNF) [200020_188406] Funding Source: Swiss National Science Foundation (SNF)
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A palladium-catalyzed Barbier allylation/translactonization cascade reaction was developed for the rapid construction of a key motif in sesquiterpenes, showing a broad substrate scope and enabling the synthesis of two paraconic acids and two 1,10-seco-guaianolides in a protecting-group-free total synthesis approach.
A palladium-catalyzed Barbier allylation/translactonization cascade reaction was established for the rapid construction of beta,gamma-disubstituted alpha-exo-methylene-gamma-butyrolactone, an important motif in sesquiterpenes. Dimethyl zinc played significant roles in both steps for the umpolung of pi-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.
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