Total synthesis of (-)-crinipellin A

Journal of the American Chemical Society

Volumn 136, Issue 29, 2014, Pages 10274-10276

  Kang, Taek ^a   Song, Seog Boem ^a   Kim, Won Yeob ^a   Kim, Byung Gyu ^a   Lee, Hee Yoon ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOADDITION;

ABSOLUTE STEREOCHEMISTRY; ALLENYL; CYCLOADDITION REACTION; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

CRINIPELLIN A; CYCLOPENTANE; NATURAL PRODUCT; UNCLASSIFIED DRUG; AZO COMPOUND; CYCLOPENTANE DERIVATIVE; DITERPENE; METHANE; TRIMETHYLENEMETHANE;

ARTICLE; CYCLOADDITION; DEPROTECTION REACTION; DESILYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROXYLATION; OXIDATION; SHARPLESS EPOXIDATION; STEREOCHEMISTRY; ANALOGS AND DERIVATIVES; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

AZO COMPOUNDS; CYCLOADDITION REACTION; CYCLOPENTANES; DITERPENES; METHANE; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84904865658     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5054412     Document Type: Article

References (39)

1. Kupta, J.; Anke, T.; Oberwinkler, F.; Schramm, G.; Steglich, W. J. Antibiot. 1979, 32, 130-135
2. Anke, T.; Heim, J.; Knoch, F.; Mocek, U.; Steffan, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1985, 24, 709-711
3. Li, Y.-Y.; Shen, Y.-M. Helv. Chim. Acta 2010, 93, 2151-2157
4. Shinohara, C.; Chikanish, T.; Nakashima, S.; Hashimoto, A.; Hamanaka, A.; Endo, A.; Hasumi, K. J. Antibiot. 2000, 53, 262-268
5. Schwartz, C. E.; Curran, D. P. J. Am. Chem. Soc. 1990, 112, 9272-9284
6. Mehta, G.; Rao, K. S.; Reddy, M. S. J. Chem. Soc. Perkin I 1991, 693-700 and references therein
7. Chen, P.; Carroll, P. J.; Sieburth, S. M. Org. Lett. 2010, 12, 4510-4512
8. Srikrishna, A.; Gowri, V. Tetrahedron 2012, 68, 3046-3055
9. Piers, E.; Renaud, J. J. Org. Chem. 1993, 58, 11-13
10. Piers, E.; Renaud, J.; Rettig, S. J. Synthesis 1998, 590-602
11. Wender, P. A.; Dore, T. M. Tetrahedron Lett. 1998, 39, 8589-8592
12. Wender, P. A. Nat. Prod. Rep. 2014, 31, 433-440
13. Wender, P. A. Tetrahedron 2013, 69, 7529-7550
14. Gaich, T.; Baran, P. S. J. Org. Chem. 2010, 75, 4657-4673
15. Lee, H.-Y.; Kim, Y. J. Am. Chem. Soc. 2003, 125, 10156-10157
16. Lee, H.-Y.; Kim, W.-Y.; Lee, S. Tetrahedron Lett. 2007, 48, 1407-1410
17. Lee, H.-Y.; Yoon, Y.; Lim, Y.-H.; Lee, Y. Tetrahedron Lett. 2008, 49, 5693-5696
18. Lee, H.-Y.; Jung, Y.; Yoon, Y.; Kim, B. G.; Kim, Y. Org. Lett. 2010, 12, 2672-2674
19. Kang, T.; Kim, W.-Y.; Yoon, Y.; Kim, B. G.; Lee, H.-Y. J. Am. Chem. Soc. 2011, 133, 18050-18053
20. Masjedizadeh, M. R.; Dannecker-Doerig, I.; Little, R. D. J. Org. Chem. 1990, 55, 2742-2752
21. Little, R. D.; Masjedizadeh, M. R.; Moeller, K. D.; Dannecker-Doerig, I. Synlett 1992, 107-113
22. Little, R. D.; Stone, K. J. J. Am. Chem. Soc. 1983, 105, 6976-6978
23. Stone, K. J.; Little, R. D. J. Am. Chem. Soc. 1985, 107, 2495-2505
24. Williams, D. R.; Heidebrecht, R. W. J. Am. Chem. Soc. 2003, 125, 1843-1850
25. Williams, D. R.; Pinchman, J. R. Can. J. Chem. 2013, 91, 21-37
26. Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185
27. Tidwell, T. T. Synthesis 1990, 857-870
28. Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 6676-6682
29. Ohira, S. Synth. Commun. 1989, 19, 561-564
30. Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521-522
31. Fürstner, A.; Méndez, M. Angew. Chem., Int. Ed. 2003, 42, 5355-5357
32. Geum, S.; Lee, H.-Y. Org. Lett. 2014, 16, 2466-2469
33. Kaufman, G. M.; Smith, J. A.; Vander Stouw, G. G.; Shechter, H. J. Am. Chem. Soc. 1965, 87, 935-937
34. Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241-3243
35. Johnson, C. R.; Zeller, J. R. Tetrahedron 1984, 40, 1225-1233
36. Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276
37. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578
38. Parish, E. J.; Wei, T.-Y. Synth. Commun. 1987, 17, 1227-1233
39. Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1971, 10, 330-331