A divergent enantioselective synthesis of 9-J1-phytoprostane and 9-A1-phytoprostane methyl ester

European Journal of Organic Chemistry

Volumn 2014, Issue 10, 2014, Pages 2111-2119

  Porta, Alessio ^a   Chiesa, Francesco ^a   Quaroni, Marco ^a   Persico, Marco ^b   Moratti, Remigio ^b   Zanoni, Giuseppe ^a   Vidari, Giovanni ^a  

^a UNIVERSITY OF PAVIA   (Italy)

^b FONDAZIONE IRCCS POLICLINICO SAN MATTEO   (Italy)

Author keywords

Asymmetric synthesis; Natural products; Olefination; Phytoprostanes; Total synthesis

Indexed keywords

EID: 84897112220     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201301703     Document Type: Article

References (23)

1. S. Parchmann, M. J. Mueller, J. Biol. Chem. 1998, 273, 32650-32655.
2. M.-J. Mueller, Curr. Opin. Plant Biol. 2004, 7, 441-448.
3. for a recent review, see:, U. Jahn, J.-M. Galano, T. Durand, Angew. Chem. 2008, 120, 5978-6041
4. Angew. Chem. Int. Ed. 2008, 47, 5894-5955.
5. M. J. Muller, Prostaglandins Leukotrienes Essent. Fatty Acids 2010, 82, 71-81.
6. U. Jahn, J.-M. Galano, T. Durand, Prostaglandins Leukotrienes Essent. Fatty Acids 2010, 82, 83-86. For the older nomenclature system, see
7. M. J. Muller, J. Chem. Biol. 1998, 5, 323-333.
8. I. Thoma, C. Loeffler, A. K. Sinha, M. Gupta, M. Krischke, B. Steffan, T. Roitsch, M. J. Mueller, Plant J. 2003, 34, 363-375.
9. M. Krischke, C. Loeffler, M. J. Mueller, Phytochemistry 2003, 62, 351-358.
10. S. Mueller, B. Hilbert, K. Dueckershoff, T. Roitsch, M. Krischke, M. J. Mueller, S. Berger, Plant Cell 2008, 20, 768-785.
11. K. Karg, V. M. Dirsch, A. M. Vollmar, J.-L. Cracowski, F. Laporte, M. J. Mueller, Free Radical Res. 2007, 41, 25-37.
12. G. Zanoni, F. Agnelli, A. Meriggi, G. Vidari, Tetrahedron: Asymmetry 2001, 12, 1779-1784.
13. G. Zanoni, A. Porta, A. Meriggi, M. Franzini, G. Vidari, J. Org. Chem. 2002, 67, 6064-6069.
14. G. Zanoni, F. Castronovo, E. Perani, G. Vidari, J. Org. Chem. 2003, 68, 6803-6805.
15. G. W. J. Fleet, P. J. C. Harding, M. J. Whitcombe, Tetrahedron Lett. 1980, 21, 4031-4034.
16. M. Yamaguchi, I. Hirao, Tetrahedron Lett. 1983, 24, 391-394.
17. H. Seike, I. Ghosh, Y. Kishi, Org. Lett. 2006, 8, 3865-3868.
18. D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287.
19. H. A. Earl, C. J. M. Stirling, J. Chem. Soc. Perkin Trans. 2 1987, 1273-1280.
20. G. Zanoni, A. Porta, G. Vidari, J. Org. Chem. 2002, 67, 4346-4351.
21. G. Zanoni, M. Valli, L. Bendjeddou, A. Porta, P. Bruno, G. Vidari, J. Org. Chem. 2010, 75, 8311-8314.
22. [1c], and references cited therein. See also:, A. Vázquez-Romero, L. Cárdenas, E. Blasi, X. Verdaguer, A. Riera, Org. Lett. 2009, 11, 3104-3107
23. W. Perlikowska, M. Mikolajczyk, Tetrahedron: Asymmetry 2011, 22, 22.