A highly rearranged novel dilactone was the single product isolated from Baeyer-Villiger oxidation of a norketone prepared from grandiflorenic acid, a natural kaurane diterpene. The complete 1H and 13C NMR assignment is presented for this novel compound that showed discrete in vitro antibacterial ac
A novel diterpene lactone
β Scribed by Doriguetto, Antonio C. ;Vieira, Henriete S. ;Ellena, Javier A. ;Takahashi, Jacqueline A. ;Boaventura, Maria A. D. ;Mascarenhas, Yvonne P.
- Publisher
- International Union of Crystallography
- Year
- 2002
- Tongue
- English
- Weight
- 325 KB
- Volume
- 58
- Category
- Article
- ISSN
- 1600-5368
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3C-NMR: 87.2 ppm) indicated that 1 was a modified kaurenoid with the Me group at C(10) shifted to C(9) . It was, therefore, identified as the 10-hydroxy-13-methoxy-9methyl-1 5-oxo-20-norkaur-16-en-18-0ic acid y-lactone. Further 2D-NMR experiments (COSY, HMBC and HMQC) allowed us the full assignment
The oxidation of a,@unsatumted ketones with pemcids is known to yield enol and/or epoxy esters or lactones depending on the reaction conditions and on whether the enone is alicyclic or acyclic \*. For example, we have found that treatment of methyl (+)-I 3-oxo-deisopropylideneneoabietate I (obtained