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

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• α-Methylene cycloalkanones are recognized for their significant biological activities.
• The synthesis and characterization of (±) HomoSarkomycine Esters are reported.

Purpose of the Study:

• To describe a novel synthetic route for (±) HomoSarkomycine Esters.
• To investigate the reaction mechanism and electronic properties using DFT studies.

Main Methods:

• The synthesis employed a Johnson-Claisen rearrangement utilizing Bylis-Hillman adducts, triethyl orthoacetate, and propanoic acid.
• Optimized reaction conditions were developed to achieve moderate yields.

Main Results:

• A small library of target compounds, (±) HomoSarkomycine Esters, was successfully synthesized.
• The reaction mechanism was elucidated, and a DFT study was performed.

Conclusions:

• The developed methodology offers efficient access to 2-hydroxymethyl-2-cyclopentenone 1a.
• This intermediate serves as a valuable precursor for the synthesis of (±) HomoSarkomycine Esters.