Enantioselective Total Synthesis of the Proposed Structure of the Endophytic Fungal Metabolite Phomolide G: Structural Revision and Unambiguous Stereochemical Assignment

European Journal of Organic Chemistry

Volumn 2016, Issue 4, 2016, Pages 688-692

  McNulty, James ^a   McLeod, David ^a   Jenkins, Hilary A ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

Asymmetric synthesis; Macrolactones; Nonenolides; Polyketides; Total synthesis

Indexed keywords

EID: 84955460259     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201501592     Document Type: Article

References (49)

1. The nonenolide class of macrolactones are also referred to as decanolides; for general reviews, see:
2. G. Drager, A. Kirschning, R. Thiericke, M. Zerlin, Nat. Prod. Rep. 1996, 13, 365 –375.
3. V. B. Riatto, R. A. Pilli, M. M. Victor, Tetrahedron 2008, 64, 2279 –2300.
4. V. Rukachaisirikul, S. Pramjit, C. Pakawatchi, M. Isaka, S. Supothina, J. Nat. Prod. 2004, 67, 1953 –1955.
5. P. Jangili, C. G. Kumar, Y. Poornachandra, B. Das, Synthesis 2015, 47, 653 –658.
6. S. Lu, T. Kurtan, G. Yang, P. Sun, A. Mandi, K. Krohn, S. Draeger, B. Schulz, Y. Yi, L. Li, W. Zhang, Eur. J. Org. Chem. 2011, 5452 –5459.
7. A. Cimmino, M. Masi, M. Evidente, S. Superchi, A. Evidente, Nat. Prod. Rep., DOI: doi/10.1039/c5np00081e.
8. J. F. Rivero-Cruz, M. Macias, C. M. Cerda-Garcia-Rojas, R. Mata, J. Nat. Prod. 2003, 66, 511 –514.
9. S. Grabley, E. Granzer, K. Hutter, D. Ludwig, M. Mayer, R. Thiercke, G. Till, J. Wink, S. Philipps, A. Zeek, J. Antibiot. 1992, 45, 56 –65.
10. Y.-Y. Li, M.-Z. Wang, Y.-J. Huang, Y.-M. Shen, Mycology 2010, 1, 254 –261.
11. N. T. Heip, Y.-H. Choi, N. Kim, S. S. Hong, S.-B. Hong, B. Y. Hwang, H.-J. Lee, S.-J. Lee, D. S. Jang, D. Lee, J. Nat. Prod. 2012, 75, 2045 –2046.
12. S. Lu, T. Kurtan, G. Yang, P. Sun, A. Mandi, K. Krohn, S. Draeger, B. Schulz, Y. Yi, L. Li, W. Zhang, Eur. J. Org. Chem. 2011, 5452 –5459.
13. A. Cimmino, A. Andolfi, S. Findevilla, M. A. Abouzeid, D. Rubiales, A. Evidente, J. Agric. Food Chem. 2012, 60, 5273 –5278.
14. A. Evidente, R. Lanzeta, R. Capasso, M. Vurro, A. Bottalico, Phytochemistry 1993, 34, 999 –1003.
15. For select examples of previous total syntheses and approaches to nonenolides, see: phomolide G:
16. P. Ramesh, B. C. Reddy, H. M. Meshram, Tetrahedron Lett. 2012, 53, 3735 –3738.
17. B. V. Subba Reddy, P. Sivaramakrishna Reddy, B. Phaneendra Reddy, J. S. Yadav, Synlett 2014, 25, 501 –504.seimatopolide A:
18. B. Schmidt, O. Kunz, M. H. Petersen, J. Org. Chem. 2012, 77, 10897 –10906.
19. K. R. Prasad, O. Revu, J. Org. Chem. 2014, 79, 1461 –1466.
20. C. Raji Reddy, N. Narichmha Rao, M. Damoder Reddy, Eur. J. Org. Chem. 2012, 4910 –4913. decarestrictine D:
21. M. B. Andrus, T.-L. Shih, J. Org. Chem. 1996, 61, 8780 –8785.
22. R. A. Pilli, M. M. Victor, Tetrahedron Lett. 1998, 39, 4421 –4424.
23. S. Colle, C. Taillefumier, Y. Chapleur, R. Liebl, A. Schmidt, Bioorg. Med. Chem. 1999, 7, 1049 –1057.
24. M. Binanzer, G. Y. Fang, V. K. Aggarwal, Angew. Chem. Int. Ed. 2010, 49, 4264 –4268 Angew. Chem. 2010, 122, 4360.nonenolide:
25. D. K. Mohapatra, D. K. Ramesh, M. A. Giardello, M. S. Chorghade, M. K. Gurjar, R. H. Grubbs, Tetrahedron Lett. 2007, 48, 2621 –2625. cytospolide E:
26. P. M. Vadhadiya, J. K. Rout, C. V. Ramana, Tetrahedron 2015, 71, 9088 –9094. pinolide: see ref.[2b]; pinolidoxin:
27. D. Liu, S. A. Kozmin, Org. Lett. 2002, 4, 3005 –3007.
28. O. Mitsunobu, Synthesis 1981, 1, 1 –28.
29. D. L. Hughes, Org. React. 1992, 42, 335 –656.
30. S. Fletcher, Org. Chem. Front. 2015, 2, 739 –752.
31. Y. Nagao, Y. Hagiwara, T. Kumagai, M. Ochirai, J. Org. Chem. 1986, 51, 2391 –2393.
32. A. González, J. Aiguadé, F. Urpí, J. Vilarrasa, Tetrahedron Lett. 1996, 37, 8949.
33. X. Ariza, J. Garcia, P. Romea, F. Urpf, Synthesis 2011, 14, 2175 –2191.
34. G. L. Khatik, V. Kumar, V. A. Nair, Org. Lett. 2012, 14, 2442 –2445.
35. G. A. Molander, J. C. McWilliams, B. C. Noll, J. Am. Chem. Soc. 1997, 119, 1265 –1276.
36. M. Reid, D. J. Rowe, R. J. K. Taylor, Chem. Commun. 2003, 2284 –2285.
37. C. P. Ashcroft, P. Hellier, A. Pettman, S. Watkinson, Org. Process Res. Dev. 2011, 15, 98 –103.
38. J. McNulty, C. Zepeda-Velazquez, D. McLeod, Green Chem. 2013, 15, 3146 –3149.
39. C. R. Sarko, I. C. Guch, M. DiMare, J. Org. Chem. 1994, 59, 705 –706.
40. K. Mikami, M. Shimizu, H.-C. Zhang, B. E. Maryanoff, Tetrahedron 2001, 57, 2917 –2951.
41. A. Matsumoto, K. Asano, S. Matsubara, Synlett 2015, 26, 1872 –1874.
42. G. Rousseau, J. M. Conia, Tetrahedron Lett. 1981, 22, 649 –652.
43. Y. Oikawa, T. Tanaka, K. Horita, O. Yonemitsu, Tetrahedron Lett. 1984, 25, 5397 –5400.
44. T. Yoshino, Y. Nagata, E. Itoh, M. Hashimoto, T. Katoh, S. Terashima, Tetrahedron 1997, 53, 10239 –10252.
45. A. Vincent, J. Prunet, Tetrahedron Lett. 2006, 47, 4075 –4077.
46. J. R. Parikh, W. v. E. Doering, J. Am. Chem. Soc. 1967, 89, 5505 –5507.
47. A. B. Smith III, I. G. Safonov, R. M. Corbett, J. Am. Chem. Soc. 2002, 124, 11102.
48. J. McNulty, A. Capretta, V. Laritchev, J. Dyck, A. J. Robertson, Angew. Chem. Int. Ed. 2003, 42, 4051 –4054 Angew. Chem. 2003, 115, 4185.
49. X. Liao, Y. Wu, J. K. De Brabander, Angew. Chem. Int. Ed. 2003, 42, 1648 –1652 Angew. Chem. 2003, 115, 1686.