Structural Diversity from the Transannular Cyclizations of Natural Germacrone and Epoxy Derivatives: A TheoreticalExperimental Study
摘要：
Treatment of germacrone (1) with different electrophiles, and of its epoxy derivatives germacrone-4,5-epoxide (2), germacrone-1,10-epoxide (3) and isogermacrone-4,5-epoxide (4) with Brnsted/Lewis acids and TiIII, gives rise to a great structural diversity. Thus, by using a maximum of two steps, the production of more than 40 compounds corresponding to 14 skeletons is described. Computational calculations rationalizing the structural divergence produced are also described. Finally, since some of the compounds generated are bioactive natural sesquiterpenes, the mechanisms of formation of these substances will provide new insights in their biosynthesis.
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DOI：
10.1002/chem.201300662
被引量：
年份：
2013
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