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Addressing the Chemistry of Germacrene A by Isotope Labeling Experiments.

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Despite the central role of germacrene A in sesquiterpene biosynthesis and its widespread occurrence in nature, its complete NMR characterization is still pending. This problem was solved through enzymatic preparation… Click to show full abstract

Despite the central role of germacrene A in sesquiterpene biosynthesis and its widespread occurrence in nature, its complete NMR characterization is still pending. This problem was solved through enzymatic preparation of germacrene A isotopomers that allowed for a full signal assignment to all three conformers. The obtained materials gave insights into the stereochemical course of the Cope rearrangement to β-elemene and uncovered the Cope rearrangement as a new EI-MS fragmentation reaction.

Keywords: isotope labeling; addressing chemistry; germacrene; chemistry; chemistry germacrene; germacrene isotope

Journal Title: Organic letters
Year Published: 2019

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