Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 39, Pages 8482-8486Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob01769a
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Funding
- DFG [DI1536/7-2]
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The non-canonical fungal alpha-humulene synthase was studied in terms of its stereochemical processes with isotopic labelling experiments. A new desymmetrisation strategy was developed to allow for a full stereochemical analysis from stereoselectively labelled farnesyl diphosphate to the achiral alpha-humulene product.
The non-canonical fungal alpha-humulene synthase was investigated through isotopic labelling experiments for its stereochemical course regarding inversion or retention at C-1, the face selectivity at C-11, and the stereoselectivity of the final deprotonation. A new and convenient desymmetrisation strategy was developed to enable a full stereochemical analysis of the catalysed steps to the achiral alpha-humulene product from stereoselectively labelled farnesyl diphosphate.
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