Study Toward the Synthesis of Gweicurculactone

Section: Research Article
Issue
Vol. 35 No. 3 (2026): Volume 35, Issue 3
Pages
106-114

Keywords:

Terpenoids, Tropon, Sesquiterpene, Dearomatization, NHC

Abstract

In this work significant progress towards the synthesis of sesquiterpene lactone (SL) which have been used to prepare Gweicurculactone using an N-heterocyclic carbene (NHC). Starting from the aldehyde compound 2 that convert to compound 4 through Wittig reaction follow by hydrogenation. Protection the phenol group using TBS-Cl to achieve compound 5. The ester was converted to an aldehyde 6 using DIBAL-H. The Henry reaction was applied on compound 6 with nitromethane in present TMG as a catalyst to produce nitro alcohol compound 7. Compound 8 was prepared after removing water molecule using Methane sulfonyl chloride in present of triethyl amine at -78 ᵒC. Methylation on the nitroalkene 8 using Methyl lithium and cupper iodide at -78 ᵒC obtain compound 9. After deprotection of 9 with tetrabutylammonium fluoride at room temperature to afford compound 10. The key tropon compound 11 framework which was made from intermolecular cyclization dearomatization through single electron transfer using potassium ferrocyanide.

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Author

Nameer S. Ezzat

University of Mosul

Identifiers

DOI: 10.33899/jes.v35i3.61630

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[1]
“Study Toward the Synthesis of Gweicurculactone”, JES, vol. 35, no. 3, pp. 106–114, Jul. 2026, doi: 10.33899/jes.v35i3.61630.
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How to Cite

[1]
“Study Toward the Synthesis of Gweicurculactone”, JES, vol. 35, no. 3, pp. 106–114, Jul. 2026, doi: 10.33899/jes.v35i3.61630.