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A Short Route to the Ester (±) HomoSarkomycin via Johnson-Claisen Rearrangement

[ Vol. 14 , Issue. 3 ]

Author(s):

Mαhamed Saied, Rafik Gatri*, Abdullah Sulaiman Al-Ayed, Youssef Arfaoui and Mohamed Moncef El Gaied   Pages 181 - 185 ( 5 )

Abstract:


Background: α-Methylene cycloalkanones are considered of interest because of their biological activity. Herein, in this paper the synthesis of (±) HomoSarkomycine Esters was described and characterized.

Methods: Using Bylis-Hillman adducts, triethlorthoacetate and propanoic acid, (±) HomoSarkomycine Esters could be synthesized by smoothly Johnson-Claisen rearrangement.

Results: A small library of target compounds was prepared under optimized reaction conditions in moderate yields. The reaction mechanism and the DFT study have been investigated.

Conclusion: This methodology provides ready access to 2-hydroxymethyl-2-cyclopentenone 1a which can be served as the raw materials of the synthesis of (±) HomoSarkomycine Ester.

Keywords:

Baylis-Hillman reaction, homosarkomycine, 2-hydroxymethylcyclopentenone, Johnson-Claisen rearrangement.

Affiliation:

Département de Chimie, Faculté des Sciences de Tunis Laboratoire de Synthèse Organique et Hétérocyclique, Campus Universitaire, Université Tunis El Manar 2, 2092 Tunis, Department of Chemistry, College of Sciences and Arts at Ar Rass, Qassim University, P.O. Box: 51477, Buraydah, Chemistry Department, College of Science and Arts at Ar Rass, Qassim University, Burayadah 51477, Unité Physico Chimie des Matériaux Condensés - UR11ES19 , Faculté des Sciences de Tunis, Campus Universitaire, Université Tunis El Manar 2, 2092 Tunis

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