Synthesis of dl-Sarkomycin (2-Methylenecyclopentanone-3-carboxylic Acid)
- 1 May 1957
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 30 (5) , 450-454
- https://doi.org/10.1246/bcsj.30.450
Abstract
dl-Sarkomycin (2-methylenecyclopentanone-3-carboxylic acid) was synthesized in a four-stage process starting from ethyl cyclopentanone-3-carboxylate, prepared by Kay’s procedure. Namely, ethyl cyclopentanone-3-carboxylate was converted into ethyl 2-(dialkylaminomethyl)-cyclopentanone-3-carboxylate and thence to ethyl 2-methylenecyclopentanone-3-carboxylate. The ester was hydrolyzed to 2-methylenecyclopentanone-3-carboxylic acid with diluted hydrochloric acid. The final product was a pale yellow oil and was effective in inhibiting the growth of Ehrlich carcinoma of mice.Keywords
This publication has 1 reference indexed in Scilit:
- SYNTHESIS AND REACTIONS OF METHYL 2-METHYL-3-OXO-1-CYCLOPENTENECARBOXYLATEThe Journal of Organic Chemistry, 1954