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

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.

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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