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Synthesis 2013; 45(12): 1693-1700
DOI: 10.1055/s-0033-1338934
DOI: 10.1055/s-0033-1338934
paper
Synthesis of (+)-Muricatacin and a Formal Synthesis of CMI-977 from l-Malic Acid
Further Information
Publication History
Received: 15 March 2013
Accepted after revision: 16 April 2013
Publication Date:
08 May 2013 (online)
![](https://www.thieme-connect.de/media/synthesis/201312/lookinside/thumbnails/10.1055-s-0033-1338934-1.jpg)
Abstract
A total synthesis of (+)-muricatacin and a formal synthesis of CMI-977 have been achieved using commercially available l-malic acid based on our furan approach to oxacyclic systems, the proven scope of which is thus broadened.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1a González M, Gándara Z, Covelo B, Gómez G, Fall Y. Tetrahedron Lett. 2011; 52: 5983
- 1b Kumarasway G, Ramakrishna D, Santhakumar K. Tetrahedron: Asymmetry 2010; 21: 544
- 1c Ghosal P, Kumar V, Shaw AK. Carbohydr. Res. 2010; 345: 41
- 1d Barros MT, Charmier MA. J, Maycock CD, Michaud T. Tetrahedron 2009; 65: 396
- 1e Prasad KR, Gandi V. Tetrahedron: Asymmetry 2008; 19: 2616
- 1f Ferrié L, Reymond S, Capdevielle P, Cossy J. Synlett 2007; 2891
- 1g Prasad KR, Anbarasan P. Tetrahedron: Asymmetry 2006; 17: 2465
- 1h Ahmed MdM, Cui H, O’Doherty GA. J. Org. Chem. 2006; 71: 6686
- 1i Popsavin V, Krstić I, Popsavin M, Srećo B, Benedeković G, Kojić V, Bogdanović G. Tetrahedron 2006; 62: 11044
-
1j Quinn KJ, Isaacs AK, Arvary RA. Org. Lett. 2004; 6: 4143
- 1k Cavé A, Chaboche C, Figadère B, Harmange JC, Laurens A, Peyrat JF, Pichon M, Szlosek M, Cotte-Lafitte J, Quéro AM. Eur. J. Med. Chem. 1997; 32: 617
- 1l Csákÿ AG, Moreno A, Navarro C, Murcia MC. Curr. Org. Chem. 2010; 14: 15
- 2a Sharma GV. M, Punna S, Rajendra Prasad T, Krishna PR, Chorgade MS, Ley SV. Tetrahedron: Asymmetry 2005; 16: 1113
- 2b Sharma GV. M, Punna S, Krishna PR, Chorghade MS, Ley SV. Tetrahedron: Asymmetry 2005; 16: 1125
- 2c Gurjar MK, Murugaiah AM. S, Radhakrishna P, Ramana CV, Chorghade MS. Tetrahedron: Asymmetry 2003; 14: 1363
- 3a Canoa P, Gándara Z, Pérez M, Gago R, Gómez G, Fall Y. Synthesis 2011; 431
- 3b Álvarez C, Pérez M, Zúñiga A, Gómez G, Fall Y. Synthesis 2010; 3883
- 3c Canoa P, Pérez M, Covelo B, Gómez G, Fall Y. Tetrahedron Lett. 2007; 48: 3441
- 3d García I, Gómez G, Teijeira M, Terán C, Fall Y. Tetrahedron Lett. 2006; 47: 1333
- 3e Teijeira M, Suárez PL, Gómez G, Terán C, Fall Y. Tetrahedron Lett. 2005; 46: 5889
- 3f Alonso D, Pérez M, Gómez G, Covelo B, Fall Y. Tetrahedron 2005; 61: 2021
- 3g Pérez M, Canoa P, Gómez G, Terán C, Fall Y. Tetrahedron Lett. 2004; 45: 5207
- 3h Fall Y, Vidal B, Alonso D, Gómez G. Tetrahedron Lett. 2003; 44: 4467
- 4a Canoa P, Vega N, Pérez M, Gómez G, Fall Y. Tetrahedron Lett. 2008; 49: 1149
- 4b Kocienski PJ, Brown RC, Pommier A, Procter M, Schmidt B. J. Chem. Soc., Perkin Trans. 1 1998; 9
- 5 For a synthesis of butenolide 17, see: Szlosek M, Franck X, Figadère B, Cave A. J. Org. Chem. 1998; 63: 5169
- 6a González M, Gándara Z, Pazos G, Gómez G, Fall Y. Synthesis 2013; 45: 625
- 6b Teijeira M, Suárez P-L, Gómez G, Terán C, Fall Y. Tetrahedron Lett. 2005; 46: 5889
- 7 Crystallographic data were collected on a Bruker Smart 1000 CCD diffractometer at CACTI (Universidade de Vigo) at 20 °C using graphite monochromated MoKα radiation (λ = 0.71073 Å), and were corrected for Lorentz and polarisation effects. The frames were integrated with the Bruker SAINT software package and the data were corrected for absorption using the program SADABS. The structures were solved by direct methods using the program SHELXS97. All non-hydrogen atoms were refined with anisotropic thermal parameters by full-matrix least-squares calculations on F2 using the program SHELXL97. Hydrogen atoms were inserted at calculated positions and constrained with isotropic thermal parameters. The structural data have been deposited with the Cambridge Crystallographic Data Centre (CCDC) with reference number CCDC 826376. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ [FAX: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].
- 8a Barton DH. R, Dorchak J, Jaszberenyl JC. Tetrahedron 1992; 48: 7435
- 8b Barton DH. R, McCombie SW. J. Chem. Soc., Perkin Trans. 1 1975; 1574
- 9 Zúñiga A, Pérez M, González M, Gómez G, Fall Y. Synthesis 2011; 3301
- 10 Müller S, Liepold B, Roth GJ, Bestmann J. Synlett 1996; 521
For recent synthesis of muricatacin, see:
For a study of the structure-activity relationships of muricatacin and analogues, see:
For a recent review on the synthesis of muricatacin and related compounds, see:
For recent syntheses of CMI-977, see: