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Deceptive Complexity in Formation of Cleistantha-8,12-diene
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https://doi.org/10.1021/acs.orglett.2c00680Abstract
A barley diterpene synthase (HvKSL4) was found to produce (14S)-cleistantha-8,12-diene (1). Formation of the nearly planar cyclohexa-1,4-diene configuration leaves the ring poised for aromatization, but necessitates a deceptively complicated series of rearrangements steered through a complex energetic landscape, as elucidated here through quantum chemical calculations and labeling studies.
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