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Synthesis 2013; 45(14): 2034-2042
DOI: 10.1055/s-0033-1338801
DOI: 10.1055/s-0033-1338801
paper
Synthesis of Conformationally Restricted Symmetric Macrodiolides via Carbonyl Ylides
Weitere Informationen
Publikationsverlauf
Received: 15. Januar 2013
Accepted after revision: 18. April 2013
Publikationsdatum:
29. Mai 2013 (online)
This paper is dedicated with best wishes to Professor Goverdhan Mehta on the occasion of his 70th birthday.
Abstract
Reaction of bis-diazocarbonyl compounds and dicarbaldehyde/divinyl derivatives in the presence of rhodium(II) acetate dimer as the catalyst led to the facile synthesis of conformationally restricted symmetric macrodiolides incorporating oxa/dioxa-bridged bicyclic systems. The structure and configuration of a representative macrodiolide were unequivocally confirmed using single-crystal X-ray analysis.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a Doyle MP, McKervey MA, Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides. Wiley-Interscience; New York: 1998
- 1b Regitz M, Mass G. Diazo Compounds: Properties and Synthesis. Academic; New York: 1986
- 1c Zhang Z, Wang J. Tetrahedron 2008; 64: 6577
- 2a Hodgson DM, Labande AH, Muthusamy S. Org. React. 2013; 80: 133
- 2b Mehta G, Muthusamy S. Tetrahedron 2002; 58: 9477
- 2c Padwa A, Weingarten MD. Chem. Rev. 1996; 96: 223
- 3 Padwa A. Tetrahedron 2011; 67: 8052 ; and references cited therein
- 4a Kang EJ, Lee E. Chem. Rev. 2005; 105: 4348
- 4b Gerbino DC, Scoccia J, Koll LC, Mandolesi SD, Podesta JC. Organometallics 2012; 31: 662
- 4c Salunke GB, Shivakumar I, Gurjar MK. Tetrahedron Lett. 2009; 50: 2048
- 5a Takahashi S, Souma K, Hashimoto R, Koshino H, Nakata T. J. Org. Chem. 2004; 69: 4509
- 5b Metz P. Top. Curr. Chem. 2005; 244: 215
- 6a Driggers EM, Hale SP, Jinbo Lee J, Terrett NK. Nat. Rev. Drug Discovery 2007; 7: 608
- 6b Marsault E, Peterson ML. J. Med. Chem. 2011; 54: 1961
- 7 Veber DF, Johnson SR, Cheng H.-Y, Smith BR, Ward KW, Kopple KD. J. Med. Chem. 2002; 45: 2615
- 8a Muthusamy S, Gnanaprakasam B, Suresh E. Org. Lett. 2005; 7: 4577
- 8b Muthusamy S, Krishnamurthi J, Nethaji M. Chem. Commun. 2005; 3862
- 8c Muthusamy S, Gnanaprakasam B. Tetrahedron 2005; 61: 1309
- 8d Muthusamy S, Babu SA, Gunanathan C, Ganguly B, Suresh E, Dastidar P. J. Org. Chem. 2002; 67: 8019
- 8e Muthusamy S, Babu SA, Gunanathan C, Suresh E, Dastidar P, Jasra RV. Tetrahedron 2001; 57: 7009
- 9a Muthusamy S, Gnanaprakasam B, Suresh E. Org. Lett. 2006; 8: 1913
- 9b Muthusamy S, Gnanaprakasam B. Tetrahedron 2007; 63: 3355
- 9c Muthusamy S, Srinivasan P. Tetrahedron Lett. 2009; 50: 3794
- 9d Muthusamy S, Karikalan T, Suresh E. Tetrahedron Lett. 2011; 52: 1934
- 10 Mottet C, Hamelin O, Garavel G, Deprés J.-P, Greene AE. J. Org. Chem. 1999; 64: 1380
- 11 Pollet P, Gelin S. Synthesis 1978; 142
- 12 Muthusamy S, Babu SA, Gunanathan C, Suresh E, Dastidar P, Jasra RV. Tetrahedron 2000; 56: 6307
- 13 Muthusamy S, Babu SA, Gunanathan C. Tetrahedron Lett. 2002; 43: 3931
- 14 CCDC-900352 (for 10a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.