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Updated: Oct 25, 2026

Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Structural Revision of the Pyrone Natural Product Syzysamalactone via Synthesis
Raju Dupud1,2, Dilna Fathima1,2, Sahla Latheef1
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad500007, India.
Abstract:
The first synthesis of the proposed structure of a neuroprotective natural product, syzysamalactone, was accomplished starting from 4-ethylcyclohexane-1,3-dione. The synthesis features a one-pot Michael addition annulation cascade to 2-pyrone in water as a solvent. The spectral data of the synthetic product did not match the reported data, indicating the need for structural revision. A significant difference in the chemical shift of the carbonyl carbon suggested a 4-pyrone skeleton, which was subsequently confirmed by synthesis. The racemic mixture was resolved by chiral HPLC, and the natural product was assigned the (S, S) configuration by XRD analysis of its 4-nitrobenzoate ester.
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