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

ABSTRACT: Background:?-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.

SUBMITTER: Saied M

PROVIDER: S-EPMC5759048 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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A Short Route to the Ester (±) HomoSarkomycin <i>via</i> Johnson-Claisen Rearrangement.

Saied M M Gatri Rafik R Al-Ayed Abdullah Sulaiman AS Arfaoui Youssef Y El Gaied Mohamed Moncef MM

Letters in organic chemistry 20170301 3

<h4>Background</h4>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.<h4>Methods</h4>Using Bylis-Hillman adducts, triethlorthoacetate and propanoic acid, (±) HomoSarkomycine Esters could be synthesized by smoothly Johnson-Claisen rearrangement.<h4>Results</h4>A small library of target compounds was prepared under optimized reaction conditions in moderate yie ...[more]

PMID: 29399007

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