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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

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

Author(s): Mαhamed Saied, Rafik Gatri*, Abdullah Sulaiman Al-Ayed, Youssef Arfaoui and Mohamed Moncef El Gaied

Volume 14, Issue 3, 2017

Page: [181 - 185] Pages: 5

DOI: 10.2174/1570178614666161230123513

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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.

Graphical Abstract

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