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A short synthesis of dimethyl tricyclo[3.3.0.0 3,7 ]octane‐1,5‐dicarboxylate and its 3,7‐dimethyl derivative. A new route to the tricyclo[3.3.0.0 3,7 ]octane skeleton

1988; Wiley; Volume: 121; Issue: 4 Linguagem: Inglês

10.1002/cber.19881210410

0009-2940

Pelayo Camps, C Borrego Iglesias, María Jesús Aira Rodríguez, María Desamparados Grancha, María Eugenia Gregori, Roberto Lozano, Miguel A. Miranda, Marta Figueredo, Ana Linares,

Asymmetric Synthesis and Catalysis

Chemische BerichteVolume 121, Issue 4 p. 647-654 Article A short synthesis of dimethyl tricyclo[3.3.0.03,7]octane-1,5-dicarboxylate and its 3,7-dimethyl derivative. A new route to the tricyclo[3.3.0.03,7]octane skeleton Pelayo Camps, Corresponding Author Pelayo Camps Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainDepartamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorCarmen Iglesias, Carmen Iglesias Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMaría Jesús Rodríguez, María Jesús Rodríguez Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMaría Desamparados Grancha, María Desamparados Grancha Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMaría Eugenia Gregori, María Eugenia Gregori Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorRoberto Lozano, Roberto Lozano Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMiguel Angel Miranda, Miguel Angel Miranda Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMarta Figueredo, Marta Figueredo Departamento de Química, Universidad Autónoma de Barcelona, Bellaterra, Barcelona, SpainSearch for more papers by this authorAna Linares, Ana Linares Laboratorio de Química Orgánica, Facultad de Farmacia, Universidad de Barcelona, Barcelona, SpainSearch for more papers by this author Pelayo Camps, Corresponding Author Pelayo Camps Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainDepartamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorCarmen Iglesias, Carmen Iglesias Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMaría Jesús Rodríguez, María Jesús Rodríguez Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMaría Desamparados Grancha, María Desamparados Grancha Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMaría Eugenia Gregori, María Eugenia Gregori Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorRoberto Lozano, Roberto Lozano Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMiguel Angel Miranda, Miguel Angel Miranda Departamento de Química Orgánica, Universitat de València, Av. Blasco Ibañez 13, 46010-València, SpainSearch for more papers by this authorMarta Figueredo, Marta Figueredo Departamento de Química, Universidad Autónoma de Barcelona, Bellaterra, Barcelona, SpainSearch for more papers by this authorAna Linares, Ana Linares Laboratorio de Química Orgánica, Facultad de Farmacia, Universidad de Barcelona, Barcelona, SpainSearch for more papers by this author First published: April 1988 https://doi.org/10.1002/cber.19881210410Citations: 16AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Abstracten Five-step syntheses of dimethyl tricyclo[3.3.0.03,7]octane-1,5-dicarboxylate (13) and its 3,7-dimethyl derivative 14 from the readily available cis-bicyclo[3.3.0]octane-3,7-diones 1 and 2, respectively, are described. The key-step implies the iodine oxidation of the bis-enolate derived from the corresponding dimethyl cis-bicyclo-[3.3.0]octane-3,7-dicarboxylates 11 and 12, thus being developed a new synthetic entry into the tricyclo[3.3.0.03,7]octane skeleton. Also, some attempts to synthesize diester 13 by using known methodology for the synthesis of compounds containing this tricyclic skeleton are described. Abstractde Eine kurze Synthese von Tricyclo [3.3.0.03,7]octan-1,5-dicarbonsäure-dimethylester und seines 3,7-Dimethylderivats. Ein neuer Weg zum Tricyclo [3.3.0.03,7]octan-Gerüst Die 5-stufige Synthese von Tricyclo[3.3.0.03,7]octan-1,5-dicarbonsäure-dimethylester (13) und seines 3,7-Dimethylderivats 14 ausgehend von den leicht zugänglichen cis-Bicyclo[3.3.0]octan-3,7-dionen 1 bzw. 2 wird beschrieben. Schlüsselreaktion ist die Oxidation der Bis-enolate der cis-Bicyclo[3.3.0]octan-3,7-dicarbonsäure-dimethylester 11 und 12 mit Iod zum Tricyclo-[3.3.0.03,7]octan-Derivat 13 bzw. 14. Zusätzlich wird die Synthese des Diesters 13 nach bekannten Methoden versucht. References 1 P. Camps, M. Figueredo, Can. J. Chem. 62 (1984) 1184. 2 Part of this work has been published in a preliminary form: P. Camps, C. Iglesias, R. Lozano, M. A. Miranda, M. J. Rodriguez, Tetrahedron Lett. 28 (1987) 1831. 3 S. H. Bertz, J. M. Cook, a. Gawish, U. Weiss, Org. Synth. 64 (1986) 27. 4 P. Camps, J. Font, J. M. Marqués, Tetrahedron 31 (1975) 2581. 5 P. Camps, Tetrahedron Lett. 1974, 4067. See also S. H. Bertz, G. Rhis, R. B. Woodward, Tetrahedron 38 (1982) 63. 6 W. Bremser, B. Franke, H. Wagner, Chemical Shifts Ranges in Carbon-13 NMR Spectroscopy, Verlag Chemie Weinheim 1982. 7 T. J. Brocksom, N. Petragnani, R. Rodrigues, H. La Scala Teixeira, Synthesis 1975, 396. 88a) H. Quast, Y. Görlach, G. Meischner, K. Peters, E. M. Peters, H. G. ovn Schnering, Tetrahedron Lett. 23 (1982) 4677. – 8b) H. Quast, Y. Görlach, E. M. Peters, K. Peters, H. G. von schnering, Ll. M. Jackman, G. Ibar, A. J. Freyer, Chem. Ber. 119 (1986) 1801. 9 P. Hofmann, E. Beck, M. D. Hoffmann, A. Sieber, Liebigs Ann. Chem. 1986, 1779. 1010a) G. W. Buhanan, C. Reyes-Zamora, P. E. Clarke, Can. J. Chem. 52 (1974) 3895. – 10b) R. van Est-Stammer, J. B. F. N. Engberts, Recl. Trav. Chim. Pays Bas 391 (1972) 1298. 11 For the synthesis of the parent hydrocarbon by this procedure see P. K. Freeman, T. D. Timothy, V. N. Mallikarjuna Rao, J. Org. Chem. 38 (1973) 3823. Citing Literature Volume121, Issue4April 1988Pages 647-654 ReferencesRelatedInformation