Bioinspired total synthesis of (±)-yezo'otogirin C

Organic Letters

Volumn 16, Issue 2, 2014, Pages 496-499

  He, Shuzhong ^a,b   Yang, Wei ^a   Zhu, Lizhi ^a   Du, Guangyan ^a   Lee, Chi Sing ^a  

^a PEKING UNIVERSITY   (China)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; TERPENE; THIOUREA; YEZO'OTOGIRIN C;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYPERICUM; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; CYCLIZATION; CYCLOHEXANONES; HYPERICUM; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM; TERPENES; THIOUREA;

EID: 84896764644     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol403374h     Document Type: Article

References (38)

1. Judd, W.; Campbell, S. C. S.; Kellogg, E. A.; Stevens, P. F. Plant Systematics -A Phylogenetic Approach; Sinauer Associates, Inc.: Sunderland, MA, 1999.
2. (a) Dostalek, M.; Pistovcakova, J.; Jurica, J.; Tomandl, J.; Linhart, I.; Sulcava, A.; Hadasova, E. Life Sci. 2005, 78, 239-244
3. Beerhues, L. Phytochemistry 2006, 67, 2201-2207.
4. Bystrov, N. S.; Chernov, B. K.; Dobrynin, V. N.; Kolosov, M. N. Tetrahedron Lett. 1975, 32, 2791-2794.
5. Chatterjee, S. S.; Bhattacharya, S. K.; Wonnemann, M.; Singer, A.; MuUer, W. E. Life Sci. 1998, 63, 499-510.
6. Guedes, A. P.; Franklin, G.; Fernandes-Ferreira, M. Phytochem. Rev. 2012, 11, 127-152.
7. Tanaka, N.; Kakuguchi, Y.; Ishiyama, H.; Kubota, T.; Kobayashi, J. Tetrahedron Lett. 2009, 50, 4747-4750.
8. Shan, M. D.; Hu, L. H.; Chen, Z. L. J. Nat. Prod. 2001, 64, 127-130.
9. For comprehensive reviews of radical cyclizations, see: (a) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519-564.
10. Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001
11. Majumdar, K. C.; Basu, P. K.; Mukhopadhyay, P. P. Tetrahedron 2005, 61, 10603-10642
12. Baralle, A.; Baroudi, A.; Daniel, M.; Fensterbank, L.; Goddard, J.-P.; Lacote, E.; Larraufie, M.-H.; Maestri, G.; Malacria, M.; Ollivier, C. In Encyclopedia of Radicals in Chemistry, Biology and Materials; Studer, A., Chatgilialoglu, C., Eds.; John Wiley & Sons: Chichester, 2012; Vol. 2, pp 729-766.
13. For reviews of Mn(III)-promoted radical cyclizations, see: (e) Snider, B. B. Chem. Rev. 1996, 96, 339-363.
14. For selected examples of Mn(OAc)3-promoted radical reactions, see: (f) Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1974, 39, 3456-3457
15. Kates, S. A.; Dombroski, M. A.; Snider, B. B. J. Org. Chem. 1990, 55, 2427-2436
16. Curran, D. P.; Morgan, T. M.; Schwartz, C. E.; Snider, B. B.; Dombroski, M. A. J. Am. Chem. Soc. 1991, 113, 6607-6617
17. Snider, B. B. Tetrahedron 2009, 65, 10738-10744
18. Taber, D. F.; Nelson, C. G. J. Org. Chem. 2011, 76, 1874-1882.
19. For reviews of CAN-promoted radical cyclizations, see: (k) Nair, V.; Mathew, J.; Prabhakaran, J. Chem. Soc. Rev. 1997, 26, 127-132
20. Nair, V.; Deepthi, A. Chem. Rev 2007, 107, 1862-1891. For selected examples of AIBN-promoted radical reactions, see:
21. (m) George, J. H.; Hesse, M. D.; Baldwin, J. E.; Adlington, R. M. Org. Lett. 2010, 12, 3532-3535.
22. (a) Yoshida, J.-i.; Nakatani, S.; Sakaguchi, K.; Isoe, S. J. Org. Chem. 1989, 54, 3383-3389
23. Qian, C. Y.; Yamada, T.; Nishino, H.; Kurosawa, K. Bull. Chem. Soc. Jpn. 1992, 65, 1371-1378.
24. (c) Yamada, T.; Iwahara, Y.; Nishino, H.; Kurosawa, K. J. Chem. Soc., Perkin Trans. 1 1993, 609-616
25. Yin, J.; Wang, C.; Kong, L.; Cai, S.; Gao, S. Angew. Chem., Int. Ed. 2012, 51, 7786-7789.
26. (e) Krabbe, S. W.; Do, D. T.; Johnson, J. S. Org. Lett. 2012, 14, 5932-5935.
27. Balci, M. Chem. Rev. 1981, 81, 91-108.
28. Spessard, S. J.; Stoltz, B. M. Org. Lett. 2002, 4, 1943-1946.
29. (a) Aubin, Y.; Audran, G.; Monti, H. Tetrahedron Lett. 2006, 47, 3669-3671
30. Saeki, M.; Toyota, M. Tetrahedron Lett. 2010, 51, 4620-4622.
31. Kuramochi, A.; Usuda, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 14200-14201.
32. Nishino, H. Top. Heterocycl. Chem 2006, 6, 39-76.
33. CCDC-924074 (13) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data-request/cif.
34. (a) Beckwith, A. L. J.; Phillipou, C.; Serelis, A. K. Tetrahedron Lett. 1981, 22, 2811-2814
35. Beckwith, A. L. J. Tetrahedron 1981, 37, 1073-3100.
36. (a) Kuramochi, A.; Usuda, H.; Yamatsugu, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 14200-14201
37. Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829-8830.
38. Porter, L. A. Chem. Rev. 1967, 67, 441.