Preparation of 2-(6-Carboxyhexyl)- and 2-(6-Methoxycarbonylhexyl)cyclopent-2-en-1-one Using Free Radical Reactions

Yu N. Ogibin; E. K. Starostin; A. V. Aleksandrov; K. K. Pivnitsky; G. I. Nikishin

doi:10.1055/s-1994-25596

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Synthesis 1994; 1994(9): 901-903
DOI: 10.1055/s-1994-25596

short paper

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Preparation of 2-(6-Carboxyhexyl)- and 2-(6-Methoxycarbonylhexyl)cyclopent-2-en-1-one Using Free Radical Reactions

Yu. N. Ogibin^* , E. K. Starostin, A. V. Aleksandrov, K. K. Pivnitsky, G. I. Nikishin

^*N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 117913, Russia

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Publication Date:
17 September 2002 (online)

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Two short and simple synthetic routes to the prostaglandin synthons 2-(6-carboxyhexyl)- and 2-(6-methoxycarbonylhexyl)cyclopent-2-en-1-one have been developed. The first is based on a cyclohexanone oxidative transformation with hydrogen peroxide and di-tert-butyl peroxide, the second on the free radical addition reaction of methyl 9-oxononanoate to acrylaldehyde diacylal.