Constructing quaternary stereogenic centers using tertiary organocuprates and tertiary radicals. Total synthesis of trans -clerodane natural products

Journal of the American Chemical Society

Volumn 137, Issue 2, 2015, Pages 660-663

  Müller, Daniel S ^a   Untiedt, Nicholas L ^a   Dieskau, André P ^a   Lackner, Gregory L ^a   Overman, Larry E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CARBON;

CARBON RADICALS; CLERODANE DITERPENOIDS; NATURAL PRODUCTS; QUATERNARY CARBON; STEREOCENTERS; STEREOGENIC CENTERS; TERTIARY RADICALS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

16 HYDROXYCLERODA 3,13 DIEN 15,16 OLIDE; AGOLACTONE; ANNONENE; BETA VINYLBUTENOLIDE; BUTENOLIDE; CLERODANE DERIVATIVE; COPPER DERIVATIVE; NAPHTHALENE DERIVATIVE; ORGANOCUPRATE DERIVATIVE; SOLIDAGOLACTONE; TRANS HYDRONAPHTHALENE; UNCLASSIFIED DRUG; BIOLOGICAL PRODUCT; COPPER; FREE RADICAL;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; CHEMISTRY TECHNIQUES, SYNTHETIC; COPPER; DITERPENES, CLERODANE; FREE RADICALS; STEREOISOMERISM;

EID: 84921440923     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja512527s     Document Type: Article

References (60)

1. Quasdorf, K. W.; Overman, L. E. Nature 2014, 516, 181-191
2. Das, J. P.; Marek, I. Chem. Commun. 2011, 47, 4593-4623
3. Hawner, C.; Alexakis, A. Chem. Commun. 2010, 46, 7295-7306
4. Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 5969-5994
5. Quaternary Stereocenters-Challenges and Solutions for Organic Synthesis; Christoffers, J.; Baro, A., Eds.; Wiley-VCH: Weinheim, 2005.
6. Schnermann, M. J.; Untiedt, N. L.; Jimenez-Oses, G.; Houk, K. N.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9581-9586
7. Iwasaki, T.; Takagawa, H.; Singh, S. P.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2013, 135, 9604-9607
8. Ren, P.; Stern, L.-A.; Hu, X. Angew. Chem., Int. Ed. 2012, 51, 9110-9113
9. Joshi-Pangu, A.; Wang, C.-Y.; Biscoe, M. R. J. Am. Chem. Soc. 2011, 133, 8478-8481
10. Hodgson, D. M.; Chung, Y. K.; Nuzzo, I.; Freixas, G.; Kulikiewicz, K. K.; Cleator, E.; Paris, J.-M. J. Am. Chem. Soc. 2007, 129, 4456-4462
11. Okada, K.; Okamoto, K.; Morita, N.; Okubo, K.; Oda, M. J. Am. Chem. Soc. 1991, 113, 9401-9402
12. Schnermann, M. J.; Overman, L. E. Angew. Chem., Int. Ed. 2012, 51, 9576-9580
13. Lackner, G. L.; Quasdorf, K. W.; Overman, L. E. J. Am. Chem. Soc. 2013, 135, 15342-15345
14. Okazaki, T.; Ohsuka, A.; Kotake, M. Nippon Kagaku Kaishi 1973, 584-589
15. Bohlman, F.; Ahmed, M.; Jakupovic, J.; King, J. M.; Robinson, H. Rev. Latinoam. Quim. 1984, 15, 16-18
16. Phadnis, A. P.; Patwardhan, S. A.; Dhaneshwar, N. N.; Tavale, S. S.; Row, T. N. G. Phytochemistry 1988, 27, 2899-2901
17. Kijjoa, A.; Pinto, M. M. M.; Hertz, W. Planta Med. 1989, 55, 205-206
18. Hara, N.; Asaki, H.; Fujimoto, Y.; Gupta, Y. K.; Singh, A. K.; Sahai, M. Phytochemistry 1995, 38, 189-194
19. Hao, X.-J.; Yang, X.-S.; Zhang, Z.; Shang, L.-J. Phytochemistry 1995, 39, 447-448
20. Ferrari, M.; Pelizzoni, F.; Ferrari, G. Phytochemistry 1971, 10, 3267-3269
21. Merritt, A. T.; Ley, S. V. Nat. Prod. Rept. 1992, 9, 243-287
22. Tokoroyama, T. Synthesis 2000, 611-633
23. Hanson, J. R. Nat. Prod. Rept. 2013, 30, 1346-1356 and earlier reviews in this series
24. Habtemariam, S.; Gray, A. I.; Waterman, P. G. Planta Med. 1992, 58, 109-110
25. Gupta, V. K.; Verma, S.; Pal, A.; Srivastava, S. K.; Srivastava, P. K.; Darokar, M. P. Appl. Microbiol. Biotechnol. 2013, 97, 9121-9131
26. Misra, P.; Sashidhara, K. V.; Singh, S. P.; Kumar, A.; Gupta, R.; Chaudhaery, S. S.; Gupta, S. S.; Majumder, H. K.; Saxena, A. K.; Dube, A. Br. J. Pharmacol. 2010, 159, 1143-1150
27. Sashidhara, K. V.; Singh, S. P.; Srivastava, A.; Puri, A.; Chhonker, Y. S.; Bhatta, R. S.; Shah, P.; Siddiqi, M. I. Eur. J. Med. Chem. 2011, 46, 5206-5211
28. Chen, C.-Y.; Chang, F.-R.; Shih, Y.-C.; Hsieh, T.-J.; Chia, Y.-C.; Tseng, H.-Y.; Chen, H.-C.; Chen, S.-J.; Hsu, M.-C.; Wu, Y.-C. J. Nat. Prod. 2000, 63, 1475-1478
29. Chang, F.-R.; Hwang, T.-L.; Yang, Y.-L.; Li, C.-E.; Wu, C.-C.; Issa, H.-H.; Hsieh, W.-B.; Wu, Y.-C. Planta Med. 2006, 72, 1344-1347
30. Lin, Y.-H.; Lee, C.-C.; Chang, F.-R.; Chang, W.-H.; Wu, Y.-C.; Chang, J.-G. Life Sciences 2011, 89, 886-895
31. Lin, Y.-H.; Lee, C.-C.; Chan, W.-L.; Chang, W.-H.; Wu, Y.-C.; Chang, J.-G. Toxicology 2011, 285, 72-80
32. Phadnis, A. P.; Patwardhan, S. A.; Dhaneshwar, N. N.; Tavale, S. S.; Row, T. N. G. Phytochemistry 1988, 27, 2899-2901
33. Hagiwara, H.; Inome, K.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1995, 757-764
34. Takahashi, S.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1979, 515-518
35. Tokoroyama, T.; Fujimori, K.; Shimizu, T.; Yamagiwa, T.; Monden, M.; Iio, H. J. Chem. Soc., Chem. Commun. 1983, 1516-1519
36. Goldsmith, D. J.; Deshpande, R. Synlett 1995, 495-497
37. Ling, T.; Poupon, E.; Rueden, E. J.; Kim, S. H.; Theodorakis, E. A. J. Am. Chem. Soc. 2002, 124, 12261-12267
38. Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586-11593
39. Commercially available on scale from Accel Pharmtech. (b) We prepared this intermediate in two steps from tetronic acid following a literature procedure, see: Cheval, N. P.; Dikova, A.; Blanc, A.; Weibel, J.-M.; Pale, P. Chem.-Eur. J. 2013, 19, 8765-8768
40. Piers, E.; Wai, J. S. M. Can. J. Chem. 1994, 72, 146-157
41. Krause, N.; Thorand, S. Inorg. Chim. Acta 1999, 296, 1-11
42. Csákÿ, A. G.; de la Herrán, G.; Murcia, M. C. Chem. Soc. Rev. 2010, 39, 4080-4102
43. Tissot, M.; Li, H.; Alexakis, A. In Copper-Catalyzed Asymmetric Synthesis; Alexakis, A.; Krause, N.; Woodward, S., Eds.; Wiley-VCH: Weinheim, 2014; chap 3.
44. Ohno, M.; Ishizaki, K.; Eguchi, S. J. Org. Chem. 1988, 53, 1285-1288
45. Mao, S.; Fang, X.; Ba, L.; Wu, F. J. Flourine Chem. 2007, 128, 5-11
46. Gong, H.; Andrews, R. S.; Zuccarello, J. L.; Lee, S. J.; Gagné, M. R. Org. Lett. 2009, 11, 879-882
47. Liu, X.-K.; Zheng, X.; Ruan, Y.-P.; Ma, J.; Huang, P.-Q. Org. Biomol. Chem. 2012, 10, 1275-1284
48. Damm, W.; Giese, B.; Hartung, J.; Hasskerl, T.; Houk, K. N.; Hueter, O.; Zipse, H. J. Am. Chem. Soc. 1992, 114, 4067-4079
49. Müller, D.; Alexakis, A. Org. Lett. 2013, 15, 1594-1597
50. Cherkauskas, J. P.; Cohen, T. J. Org. Chem. 1992, 57, 6-8
51. Cohen, T.; Zhang, B.; Cherkauskas, J. P. Tetrahedron 1994, 50, 11569-11584
52. Clayden, J.; MacLellan, P. Beilstein J. Org. Chem. 2011, 7, 582-595
53. Firouzabadi, H.; Iranpoor, N.; Jafarpour, M. Tetrahedron Lett. 2006, 47, 93-97
54. Boukouvalas, J.; Lachance, N. Synlett 1998, 31-32
55. Marcos, I. S.; Pedrero, A. B.; Sexmero, M. J.; Diez, D.; García, N.; Escola, M. A.; Basabe, P.; Conde, A.; Moro, R. F.; Urones, J. G. Synthesis 2005, 3301-3310
56. Basabe, P.; Bodero, O.; Marcos, I. S.; Diez, D.; De Roman, M.; Blanco, A.; Urones, J. G. Tetrahedron 2007, 63, 11838-11843
57. May, T. L.; Dabrowski, J. A.; Hoveyda, A. H. J. Am. Chem. Soc. 2011, 133, 736-739
58. Müller, D.; Tissot, M.; Alexakis, A. Org. Lett. 2011, 13, 3040-3043
59. Gao, F.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10961-10963
60. Cell viability was determined by Dr. Sangkil Nam at the City of Hope Comprehensive Cancer Center using a MTS metabolic activity assay as described by the supplier (Promega), see: Nam, S.; Williams, A.; Vultur, A.; List, A.; Bhalla, K.; Smith, D.; Lee, F. Y.; Jove, R. Mol. Cancer Ther. 2007, 6, 1400-1405