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- W2949551401 abstract "Publisher Summary This chapter summarizes the molecular rearrangement studies in the derivatives of grandiflorenic acid and some related diterpene ring systems. The structures and stereochemistries of all rearrangement products are determined on the basis of 1 H, 13 C-NMR spectroscopic evidence and some of them are further confirmed by X-ray crystallographic analysis. The mechanisms for their formation are presented in detail in the chapter. The initial aim of the study presented in the chapter, was to transform the diterpene acid to zoapatline and Its analogs, which had been Isolated from the native Mexican shrub Zoapatle. These diterpene lactones possess a basic skeleton In which the methyl groups at C-10 in the natural (-)-kaurane skeleton migrates to C-9. During the study, it was assumed that that they might be derived chemically from grandiflorenic acid via the acid-catalyzed rearrangement of its 9,11-epoxide. Before attempting to transform grandiflorenic acid to zoapatline, the rearrangement of the epoxides of both (-)-kaur-9(11)-en-19-oic acid and methyl (-)-kaur-9(11)-en-19-oate is investigated to see whether or not the methyl group at C-10 would migrate to C-9. During the course of this work, some very interesting rearrangement reactions were discovered, which led to the further study of the other molecular rearrangements in several derivatives of grandiflorenic acid. As a result, eight diterpenes 4, 5, 8, 17, 19, 20, 21 and 22, were prepared with new ring systems which have not been encountered in nature." @default.
- W2949551401 created "2019-06-27" @default.
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- W2949551401 date "1996-01-01" @default.
- W2949551401 modified "2023-09-27" @default.
- W2949551401 title "Molecular rearrangements in the derivatives of grandiflorenic acid [(-)-kaura-9(11),16-diene-19-oic acid] and some related diterpenes" @default.
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- W2949551401 doi "https://doi.org/10.1016/s1572-5995(96)80011-1" @default.
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