Total synthesis of (±)-maoecrystal v

Journal of the American Chemical Society

Volumn 134, Issue 45, 2012, Pages 18860-18867

  Peng, Feng ^a,c   Danishefsky, Samuel J ^a,b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^c MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CORE SYSTEMS; DIELS-ALDER CYCLIZATION; RING SYSTEMS; TOTAL SYNTHESIS;

CHEMISTRY; SYNTHESIS (CHEMICAL);

HYDROGEN;

CHEMICAL AGENT; HYDROGEN; MAOECRYSTAL V; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CRYSTAL; CYCLIZATION; CYCLOADDITION; DEHYDROGENATION; OXIDATION; PATTERN RECOGNITION; SYNTHESIS; THERMODYNAMICS;

DITERPENES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84869412367     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja309905j     Document Type: Article

References (54)

1. Sun, H. D.; Xu, Y. L.; Jiang, B. Diterpenoids from Isodon Species; Science Press: Beijing, China, October 2001.
2. Li, S. H.; Niu, X. M.; Shen, Y. H.; Zhang, H. J.; Sun, H. D.; Li, M. L.; Tian, Q. E.; Lu, Y.; Cao, P.; Zhang, Q. T. Org. Lett. 2004, 6, 4327-4330
3. Gong, J.; Lin, G.; Li, C. C.; Yang, Z. Org. Lett. 2009, 11, 4770-4773
4. Krawczuk, P. J.; Schone, N.; Baran, P. S. Org. Lett. 2009, 11, 4774-4776
5. Nicolaou, K. C.; Dong, L.; Deng, L. J.; Talbot, A. C.; Chen, D. Y. K. Chem. Commun. 2010, 46, 70-72
6. Lazarski, K. E.; Hu, D. X.; Sterm, C. L.; Thomson, R. J. Org. Lett. 2010, 12, 3010-3013
7. Singh, V.; Bhalerao, P.; Mobin, S. M. Tetrahedron Lett. 2010, 51, 3337-3339
8. Baitinger, I.; Mayer, P.; Trauner, D. Org. Lett. 2010, 12, 5656-5659
9. Gu, Z.; Zakarian, A. Org. Lett. 2011, 13, 1080-1082
10. Dong, L.; Deng, L.; Lim, Y. H.; Leugn, G. Y. C.; Chen, D. Y.-K. Chem.-Eur. J. 2011, 17, 5778-5781
11. Cha, J. Y.; Yeoman, J. T. S.; Reisman, S. E. J. Am. Chem. Soc. 2011, 133, 14964-14967
12. Gong, J.; Lin, G.; Sun, W.; Li, C.; Yang, Z. J. Am. Chem. Soc. 2010, 132, 16745-16746
13. Wilson, R. M.; Danishefsky, S. J. J. Org. Chem. 2007, 72, 4293-4305
14. Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, pp 513-550.
15. Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668-1698
16. Liao, C.; Peddinti, R. K. Acc. Chem. Res. 2002, 35, 856-866
17. Ihara, M. Chem. Pharm. Bull. 2006, 54, 765-774
18. Peng, F.; Yu, M.; Danishefsky, S. J. Tetrahedron Lett. 2009, 50, 6586-6587
19. Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. J. Am. Chem. Soc. 2000, 122, 1360-1370
20. Stork, G.; Danheiser, R. J. Org. Chem. 1973, 38, 1775
21. Still, C.; Mitra, A. J. Am. Chem. Soc. 1978, 100, 1927-1928
22. Rabideau, P. W. Tetrahedron 1989, 45, 1579-1603
23. Whitesides, G. M.; Whmann, W. J. J. Org. Chem. 1970, 35, 3565-3567
24. Williams, D. R.; Robinson, L. A.; Nevill, C. R.; Reddy, J. P. Angew. Chem., Int. Ed. 2007, 46, 915-918
25. Seeman, J. I. Chem. Rev. 1983, 83, 84-134
26. Peng, F.; Danishefsky, S. J. Tetrahedron Lett. 2011, 52, 2104-2106
27. Kondo, K.; Sodeaka, M.; Mori, M.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 4219-4223
28. Schultz, A. G.; Holoboski, M. A.; Smvth, M. S. J. Am. Chem. Soc. 1996, 118, 6210-6219
29. Schultz, A. G.; Wang, A. J. Am. Chem. Soc. 1998, 120, 8259-8260
30. Strekowski, L.; Kong, S.; Battiste, M. A. J. Org. Chem. 1988, 53, 901-904
31. Guan, Z. H.; Zuo, W.; Zhao, L. B.; Ren, Z. H.; Liang, Y. M. Synthesis 2007, 1465-1470
32. Danishefsky, S. J.; Harayama, T.; Singh, R. K. J. Am. Chem. Soc. 1979, 101, 7008-7012
33. Danishefsky, S. J.; Morris, J.; Mullen, G.; Gammill, R. J. Am. Chem. Soc. 1982, 104, 7591-7599
34. Hayashi, Y.; Rohde, J. J.; Corey, E. J. J. Am. Chem. Soc. 1996, 118, 5502-5503
35. Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808-3809
36. Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388-6390
37. Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650-1667
38. Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4435-4436
39. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370
40. Oppolzer, W.; Godel, T. J. Am. Chem. Soc. 1978, 100, 2583-2584
41. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293-4294
42. Lombardo, L. Organic Syntheses 1987, 65, 81-83
43. Rousseau, G.; Conia, J. M. Tetrahedron Lett. 1981, 22, 649-652
44. Denis, J. M.; Girard, C.; Conia, J. M. Synthesis 1972, 549-551
45. Birman, V. B.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 2080-2081
46. Mello, R.; Fiorentino, M.; Fusco, C.; Curci, R. J. Am. Chem. Soc. 1989, 111, 6749-6757
47. D'Accolti, L.; Dinoi, A.; Fusco, C.; Russo, A.; Curci, R. J. Org. Chem. 2003, 68, 7806-7810
48. Woodward first postulated that if the unhindered face of an olefin is electron-depleted, then an electron-deficient reagent might be less likely to pass over that face. Thus, in such circumstances, electronic and steric factors play competing roles, leading to the formation of diastereomeric product mixtures. See: footnote, page 6, in Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57
49. Nii, K.; Tagami, K.; Kijima, M.; Munakata, T.; Ooi, T.; Kusumi, T. Bull. Chem. Soc. Jpn. 2008, 81, 562-573
50. Jung, M. E.; Allen, D. A. Org. Lett. 2008, 10, 2039-2041
51. Falrweather, K. A.; Mander, L. N. Org. Lett. 2006, 8, 3395-3398
52. Zhou, W.-S. Huaxue Xuebao 1985, 43, 237-242
53. Sudha, R.; Narasimhan, K. M.; Waraswathy, V. G.; Sankararaman, S. J. Org. Chem. 1996, 61, 1877-1879
54. Ireland, R. E.; Hengartner, U. J. Am. Chem. Soc. 1972, 94, 3652-3653