Donor-acceptor substituted cyclopropane to butanolide and butenolide natural products: Enantiospecific first total synthesis of (+)-hydroxyancepsenolide

Organic Letters

Volumn 16, Issue 24, 2014, Pages 6424-6427

  Gharpure, Santosh J ^a   Nanda, Laxmi Narayan ^a   Shukla, Manoj Kumar ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ANTIMYCIN A1; BIOLOGICAL PRODUCT; BLASTOMYCINONE; BUTENOLIDE; CITRININ; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; GAMMA BUTYROLACTONE; HYDROXYANCEPSENOLIDE; JURUENOLIDE C; LACTONE;

ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

4-BUTYROLACTONE; ANTIMYCIN A; BIOLOGICAL PRODUCTS; CYCLOPROPANES; DIOXOLES; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84919665644     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol503246k     Document Type: Article

References (44)

1. Rao, Y. S. Chem. Rev. 1976, 76, 625
2. Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426
3. Nishida, T.; Nihira, T.; Yamada, Y. Tetrahedron 1991, 47, 6623
4. Riclea, R.; Aigle, B.; Leblond, P.; Schoenian, I.; Spiteller, D.; Dickscha, J. S. ChemBioChem 2012, 13, 1635 and references cited therein
5. Lopes, N. P.; Franca, S. D. C.; Pereira, A. M. S.; Maia, J. G. S.; Kato, M. J.; Cavalheiro, A. J.; Gottlieb, O. R.; Yoshida, M. Phytochemistry 1994, 35, 1469
6. Lopes, N. P.; Blumenthal, E. E. D. A.; Cavalheiro, A. J.; Kato, M. J.; Yoshida, M. Phytochemistry 1996, 43, 1089
7. Magri, F. M. M.; Kato, M. J.; Yoshida, M. Phytochemistry 1996, 43, 669
8. Lopes, N. P.; Silva, D. H. S.; Kato, M. J.; Yoshida, M. Phytochemistry 1998, 49, 1405
9. Lopes, N. P.; Kato, M. J.; Yoshida, M. Phytochemistry 1999, 51, 29
10. Schmitz, F. J.; Kraus, K. W.; Ciereszko, L. S.; Sifford, D. H.; Weinheimer, A. J. Tetrahedron Lett. 1966, 7, 97
11. Schitz, F. J.; Lorance, E. D.; Ciereszko, L. S. J. Org. Chem. 1969, 34, 1989
12. Schitz, F. J.; Lorance, E. D. J. Org. Chem. 1971, 36, 719
13. Rodriguez, A. D.; Ramirez, C. J. Nat. Prod. 1994, 57, 339
14. Guo, Y.-W.; Gavagnin, M.; Mollo, E.; Trivellone, E.; Cimino, G. J. Nat. Prod. 1999, 62, 1194
15. Lorenzo, M.; Brito, I.; Cueto, M.; DCroz, L.; Darias, J. Org. Lett. 2006, 8, 5001
16. Ferrarini, R. S.; Santos, A. A. D.; Comasseto, J. V. Tetrahedron 2012, 68, 8431
17. Lee, S. I.; Jang, J. H.; Hwang, G.-S.; Ryu, D. H. J. Org. Chem. 2013, 78, 770 Supporting Information contains a full list
18. Total synthesis of (+)-juruenolide C: Clive, D. L. J.; Ardelean, E. S. J. Org. Chem. 2001, 66, 4841
19. Podraza, K. F.; Sneden, A. T. J. Nat. Prod. 1985, 48, 792
20. Larson, G. L.; Perez, R. M. B. J. Org. Chem. 1985, 50, 5257
21. Trost, B. M.; Muller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985
22. Trost, B. M.; Muller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888
23. Yao, Z.-J.; Yu, Q.; Wu, Y-L. Synth. Commun. 1996, 3613
24. Furstner, A.; Dierkes, T. Org. Lett. 2000, 2, 2463
25. Takai, K.; Iriye, R. Biosci. Biotechnol. Biochem. 2001, 65, 1903
26. Yang, Y.-Q.; Yi-Kang, W. Chin. J. Chem. 2005, 23, 1519
27. Ghobril, C.; Kister, J.; Baati, R. Eur. J. Org. Chem. 2011, 3416
28. Hikosaka, G.; Hattori, Y.; Makabe, H. Tetrahedron: Asymmetry 2014, 25, 1367
29. Gharpure, S. J.; Shukla, M. K.; Vijayasree, U. Org. Lett. 2009, 11, 5466
30. Gharpure, S. J.; Nanda, L. N.; Shukla, M. K. Eur. J. Org. Chem. 2011, 6632
31. Gharpure, S. J.; Vijayasree, U.; Reddy, S. R. B. Org. Biomol. Chem. 2012, 10, 1735
32. Jones, S. B.; Simmons, B.; Mastracchio, A.; MacMillan, D. W. C. Nature 2011, 475, 183
33. Shimokawa, J. Tetrahedron Lett. 2014, 55, 6156
34. Reissig, H. U.; Zimmer, R. Chem. Rev. 2003, 103, 1151
35. Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321
36. Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051
37. Lebold, T. P.; Kerr, M. A. Pure Appl. Chem. 2010, 82, 1797
38. Melnikov, M. Y.; Budynina, E. M.; Ivanova, O. A.; Trushkov, I. V. Mendeleev Commun. 2011, 21, 293
39. Wang, Z. W. Synlett 2012, 2311
40. Tang, P.; Qin, Y. Synthesis 2012, 44, 2969
41. Cavitt, M. A.; Phun, L. H.; France, S. Chem. Soc. Rev. 2014, 43, 804
42. Schneider, T. F.; Kaschel, J.; Werz, D. B. Angew. Chem., Int. Ed. 2014, 53, 5504
43. Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900
44. Wojtkielewicz, A. Curr. Org. Synth. 2013, 10, 43