Applications of Olefination Reactions to Cassiol Synthesis

Abstract

first_page settings Order Article Reprints Font Type: Arial Georgia Verdana Font Size: Aa Aa Aa Line Spacing:    Column Width:    Background: Open AccessAbstract Applications of Olefination Reactions to Cassiol Synthesis by María I. Colombo, Jose A. Bacigaluppo, Mirta P. Mischne, Juán Zinczuk and Edmundo A. Rúveda Instituto de Química Orgánica de Síntesis (IQUIOS-UNR) Casilla de Correo 991, 2000 Rosario, Argentina Molecules 2000, 5(3), 327-329; https://doi.org/10.3390/50300327 Published: 22 March 2000 Download Download PDF Download PDF with Cover Download XML Download Epub Versions Notes Abstract: Olefination reactions directed to the synthesis of cassiol from compounds 2-5 will be discussed. IntroductionCassiol (1), which exhibits a potent antiulcer activity, contains a functionalized cyclohexenone mo-eity with a quaternary stereogenic center at C-4 and a 2-vinyl-1,3-diol chain, which is connected at the C-3 position. Because of its structural features and pharmacological activity, a number of synthesis have been recorded [1]. Our approach toward the synthesis of 1 involves the C-1’- C-2’ double bond disconnection through a carbonyl olefination procedure [2]. This sequence allow us to explore the ole-fination reaction in two differents ways, switching the polarity of the coupling partners as shown in the following scheme.By following approach a, a precursor of cassiol (1) was obtained in our laboratory, but unfortu-nately in an unsatisfactory low yield [3]. In order to improve the yield of the coupling reaction, com-pounds 2-5 were then selected for study. ExperimentalCompounds 2-5 were prepared according to standard methods. DiscussionDue to lack of success in the coupling of 4-5 with 2 and 3 by using differents conditions of solvents and bases we turned our attention to approach b.Starting with compound 4, the diol 6 has been ob-tained. Treatment of 6 with mercaptobenzothiazole provided the corresponding sulfide 7. Starting with 7 and through the corresponding sulfone 8 we hope to improve the yield of the coupling product, on the basis of the recent report of Hart and Kozikowski et al [4]. AcknowledgementsUNR, CONICET, Agencia Nacional de Promoción Cinentífica.References and NotesColombo, M.I.; Rúveda, E.A. J. Braz. Chem. Soc. 1998, 9, 303. [CrossRef] Entwistle, D. Contemporary Organic Synthesis 1997, 4, 40. Colombo, M.I.; Bacigaluppo, J.A.; Rúveda, E.A. An. Asoc. Quim. Argent. 1998, 86, 312. Hart, D.J.; Li, J.; Wu, W-L.; Kozikowski, A.P. J. Org. Chem. 1997, 62, 5023. [CrossRef] Share and Cite MDPI and ACS Style Colombo, M.I.; Bacigaluppo, J.A.; Mischne, M.P.; Zinczuk, J.; Rúveda, E.A. Applications of Olefination Reactions to Cassiol Synthesis. Molecules 2000, 5, 327-329. https://doi.org/10.3390/50300327 AMA Style Colombo MI, Bacigaluppo JA, Mischne MP, Zinczuk J, Rúveda EA. Applications of Olefination Reactions to Cassiol Synthesis. Molecules. 2000; 5(3):327-329. https://doi.org/10.3390/50300327 Chicago/Turabian Style Colombo, María I., Jose A. Bacigaluppo, Mirta P. Mischne, Juán Zinczuk, and Edmundo A. Rúveda. 2000. "Applications of Olefination Reactions to Cassiol Synthesis" Molecules 5, no. 3: 327-329. https://doi.org/10.3390/50300327 Find Other Styles Article Metrics No No Article Access Statistics For more information on the journal statistics, click here. Multiple requests from the same IP address are counted as one view.