| Structure Identification: |
| J Org Chem. 2000 Apr 7;65(7):2122-6. | | An enantioselective route to paeonilactone A via palladium- and copper-catalyzed reactions.[Pubmed: 10774035] |
METHODS AND RESULTS:
We herein report on a formal total synthesis of Paeonilactone A involving palladium-, copper-, and enzyme-catalyzed reactions starting from 1,3-cyclohexadiene. The key step in the synthesis, a palladium(II)-catalyzed 1,4-oxylactonization of a conjugated diene, simultaneously introduces two of the oxygen substituents required for the target molecule. The synthesis also includes our recently developed copper(I)-catalyzed cross-coupling reaction between dienyltriflates with Grignard reagents, introducing one of the methyl groups present in the target molecule.
CONCLUSIONS:
This new approach toward Paeonilactone A allows complete control of all four stereogenic centers and is the first enantioselective route toward Paeonilactone A starting from an achiral substrate. | | Fitoterapia. 2007 Jan;78(1):76-8. | | Monoterpene glycosides from Paeonia delavayi.[Pubmed: 17067761] |
METHODS AND RESULTS:
A new monoterpene glycoside, 4-O-methyl-4''-hydroxy-3''-methoxy-paeoniflorin (1), was isolated from the root cortex of Paeonia delavayi along with the known paeoniflorin, oxypaeoniflorin, benzoylpaeoniflorin, benzoyloxypaeoniflorin, albiflorin and a Paeonilactone A. |
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