From Stereodefined Cyclobutenes to Dienes: Total Syntheses of Ieodomycin D and the Southern Fragment of Macrolactin A

Organic Letters

Volumn 17, Issue 18, 2015, Pages 4486-4489

  Souris, Caroline ^a   Misale, Antonio ^a   Chen, Yong ^a   Luparia, Marco ^a   Maulide, Nuno ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; IEODOMYCIN A; MACROLACTIN A; MACROLIDE; POLYENE; UNSATURATED FATTY ACID;

CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CYCLOBUTANES; FATTY ACIDS, UNSATURATED; MACROLIDES; MOLECULAR STRUCTURE; POLYENES; STEREOISOMERISM;

EID: 84941899137     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02149     Document Type: Article

References (45)

1. Leukotrienes and Lipoxygenase; Rokach, J., Ed.; Elsevier: NewYork, 1989.
2. Green, R. H.; Lambeth, P. F. Tetrahedron 1983, 39, 1687-1721 10.1016/S0040-4020(01)88677-4
3. The Retinoids; Born, M. B.; Roberts, A. B.; Goodman, D. S., Eds.; Academic Press: New York, 1984; Vols. 1 and 2.
4. The Retinoids: Biology, Chemistry and Medicine, 2 nd ed.; Born, M. B.; Roberts, A. B.; Goodman, D. S., Eds.; Raven: New York, 1993.
5. Chemistry and Biology of Synthetic Retinoids; Dawson, M. L.; Okamura, W. H., Eds.; CRC Press: Boca Raton, FL, 1990.
6. Semlyen, J. A. Large Ring Molecules; Wiley: Chichester, U.K., 1996.
7. Omura, S.; Tanaka, H. In Macrolide Antibiotics: Chemistry, Biology and Practice; Omura, S., Ed.; Academic Press: New York, 1984; p 351.
8. The Chemistry of Dienes and Polyenes; Rappoport, Z., Ed.; Wiley: Chichester, U.K., 1997.
9. Nicolaou, K. C.; Snyder, S. A. Classics in Total Synthesis II: More Targets, Strategies; Wiley-VCH: Weinheim, 2003.
10. De Paolis, M.; Chataigner, I.; Maddaluno, J. Top. Curr. Chem. 2012, 327, 87-146 10.1007/128-2012-320
11. Mondol, M. M. M.; Kim, J. H.; Lee, M. A.; Tareq, F. S.; Lee, H. S.; Lee, Y. J.; Shin, H. J. J. Nat. Prod. 2011, 74, 1606-1612 10.1021/np200223r
12. Tungen, J. E.; Aursnes, M.; Hansen, T. V. Tetrahedron 2014, 70, 3793-3797 10.1016/j.tet.2014.04.020
13. Chinnababu, B.; Purushotham Reddy, S.; Kumar Reddy, D.; Chandra Rao, D.; Venkateswarlu, Y. Synthesis 2012, 2012, 311-315 10.1055/s-0031-1289640
14. Nageswara Rao, N.; Meshram, H. M. Tetrahedron Lett. 2013, 54, 4544-4546 10.1016/j.tetlet.2013.06.071
15. Souris, C.; Frébault, F.; Patel, A.; Audisio, D.; Houk, K. N.; Maulide, N. Org. Lett. 2013, 15, 3242-3245 10.1021/ol401226y
16. Souris, C.; Frébault, F.; Audisio, D.; Farès, C.; Maulide, N. Synlett 2013, 24, 1286-1290 10.1055/s-0033-1338452
17. Souris, C.; Luparia, M.; Frébault, F.; Audisio, D.; Farès, C.; Goddard, R.; Maulide, N. Chem.-Eur. J. 2013, 19, 6566-6570 10.1002/chem.201300776
18. Luparia, M.; Oliveira, M. T.; Audisio, D.; Frébault, F.; Goddard, R.; Maulide, N. Angew. Chem., Int. Ed. 2011, 50, 12631-12635 10.1002/anie.201106321
19. Audisio, D.; Gopakumar, G.; Xie, L. G.; Alves, L. G.; Wirtz, C.; Martins, A. M.; Thiel, W.; Farès, C.; Maulide, N. Angew. Chem., Int. Ed. 2013, 52, 6313-6316 10.1002/anie.201301034
20. Audisio, D.; Luparia, M.; Oliveira, M. T.; Klütt, D.; Maulide, N. Angew. Chem., Int. Ed. 2012, 51, 7314-7317 10.1002/anie.201202853
21. Niyomchon, S.; Audisio, D.; Luparia, M.; Maulide, N. Org. Lett. 2013, 15, 2318-2321 10.1021/ol401033g
22. Misale, A.; Niyomchon, S.; Luparia, M.; Maulide, N. Angew. Chem., Int. Ed. 2014, 53, 7068-7073 10.1002/anie.201309074
23. Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1988, 29, 2395-2396 10.1016/S0040-4039(00)87890-9
24. Majid, T. N.; Yeh, M. C. P.; Knochel, P. Tetrahedron Lett. 1989, 30, 5069-5072 10.1016/S0040-4039(01)93449-5
25. Dieter, R. K.; Guo, F. Org. Lett. 2008, 10, 2087-2090 10.1021/ol800727f
26. Dieter, R. K.; Picado, A. J. Org. Chem. 2014, 79, 11125-11138 10.1021/jo502111c
27. Müller, D. S.; Untiedt, N. L.; Dieskau, A. P.; Lackner, G. L.; Overman, L. E. J. Am. Chem. Soc. 2015, 137, 660-663 10.1021/ja512527s
28. Sekiya, K.; Nakamura, E. Tetrahedron Lett. 1988, 29, 5155-5156 10.1016/S0040-4039(00)80706-6
29. Harrington-Frost, N.; Leuser, H.; Calaza, M. I.; Kneisel, F. F.; Knochel, P. Org. Lett. 2003, 5, 2111-2114 10.1021/ol034525i
30. Corey, E. J.; Boaz, N. W. Tetrahedron Lett. 1984, 25, 3063-3066 10.1016/0040-4039(84)80008-8
31. Hoge, G. J. Am. Chem. Soc. 2004, 126, 9920-9921 10.1021/ja048079l
32. Smith, A. B., III; Ott, G. R. J. Am. Chem. Soc. 1996, 118, 13095-13096 10.1021/ja963543a
33. Kim, Y.; Singer, R. A.; Carreira, E. M. Angew. Chem., Int. Ed. 1998, 37, 1261-1263 10.1002/(SICI)1521-3773(19980518)37:9<1261::AID-ANIE1261>3.0.CO;2-2
34. Marino, J. P.; McClure, M. S.; Holub, D. P.; Comasseto, J. V.; Tucci, F. C. J. Am. Chem. Soc. 2002, 124, 1664-1668 10.1021/ja017177t
35. Li, S.; Donaldson, W. A. Synthesis 2003, 13, 2064-2068 10.1055/s-2003-41450
36. Bonini, C.; Chiummiento, L.; Pullez, M.; Colobert, F.; Solladié, G. J. Org. Chem. 2004, 69, 5015-5022 10.1021/jo049556l
37. Yadav, J. S.; Gupta, M.; Prathap, I. Synthesis 2007, 2007, 1343-1348 10.1055/s-2007-966010
38. Bonini, C.; Chiummiento, L.; Videtta, V.; Colobert, F.; Solladié, G. Synlett 2006, 2006, 2427-2430 10.1055/s-2006-950424
39. Lu, X. L.; Xu, Q. Z.; Liu, X. Y.; Cao, X.; Ni, K. Y.; Jiao, B. H. Chem. Biodiversity 2008, 5, 1669-1674 10.1002/cbdv.200890155
40. Gustafson, K.; Roman, M.; Fenical, W. J. Am. Chem. Soc. 1989, 111, 7519-7524 10.1021/ja00201a036
41. Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522-524 10.1002/anie.197805221
42. Dhimitruka, I.; SantaLucia, J. Org. Lett. 2006, 8, 47-50 10.1021/ol0524048
43. Hughes, D. L.; Reamer, R. A.; Bergan, J. J.; Grabowski, E. J. J. J. Am. Chem. Soc. 1988, 110, 6487-6491 10.1021/ja00227a032
44. But, T. Y. S.; Toy, P. H. Chem.-Asian J. 2007, 2, 1340-1355 10.1002/asia.200700182
45. Swamy, K. C. K.; Kumar, N. N. B.; Kumar, K. V. Chem. Rev. 2009, 109, 2551-2651 10.1021/cr800278z