Total Synthesis of (Nor)illudalane Sesquiterpenes Based on a C(sp3)-H Activation Strategy.
- Melot R Department of Chemistry , University of Basel , St. Johanns-Ring 19 , CH-4056 Basel , Switzerland.
- Craveiro MV Department of Chemistry , University of Basel , St. Johanns-Ring 19 , CH-4056 Basel , Switzerland.
- Baudoin O Department of Chemistry , University of Basel , St. Johanns-Ring 19 , CH-4056 Basel , Switzerland.
- 2019-07-20
Published in:
- The Journal of organic chemistry. - 2019
English
Three (nor)illudalane sesquiterpenes were synthesized from a common intermediate in racemic and enantioenriched forms using Pd0-catalyzed C(sp3)-H arylation as a key step. The configuration of the isolated, highly symmetric quaternary stereocenter of the target molecules was controlled through a matched combination of chiral substrate and catalyst. Moreover, the recently developed Ir-catalyzed C-H borylation/Cu-catalyzed methylation method was employed to install the methyl group on the benzene ring. This strategy allowed the efficient synthesis of both racemic and (S)-configured puraquinonic acid, deliquinone, and russujaponol F.
- Language
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- English
- Open access status
- green
- Identifiers
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- DOI 10.1021/acs.joc.9b01669
- PMID 31322348
- Persistent URL
- https://sonar.ch/global/documents/231987
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