(+)- And (-)-mutisianthol: First total synthesis, absolute configuration, and antitumor activity

Journal of Organic Chemistry

Volumn 74, Issue 6, 2009, Pages 2561-2566

  Bianco, Graziela G ^a   Ferraz, Helena M C ^a   Costas, Arinice M ^b   Costa Lotufo, Letícia V ^b   Pessoa, Claudia ^b   De Moraes, Manoel O ^b   Schreins, Marcus G ^c   Pfaltz, Andreas ^c   Silva Jr , Luiz F ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^c UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATIONS; ANTI-TUMOR ACTIVITIES; HUMAN TUMOR CELLS; IRIDIUM CATALYSTS; NATURAL PRODUCTS; RING CONTRACTIONS; SESQUITERPENE; TARGET MOLECULES; TOTAL SYNTHESIS;

CELL CULTURE; IRIDIUM; OLEFINS; THALLIUM;

IODINE;

1,2 DIHYDRONAPHTHALENE; 2 METHYLANISOLE; ALKENE; ANISOLE DERIVATIVE; DOXORUBICIN; IODINE; IRIDIUM; MUTISIANTHOL; NAPHTHALENE DERIVATIVE; PLANT EXTRACT; SESQUITERPENE DERIVATIVE; THALLIUM; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CONTROLLED STUDY; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HUMAN; HUMAN CELL; HYDROGENATION; MEDICINAL PLANT; MUTISIA HOMOEANTHA; STRUCTURE ACTIVITY RELATION;

ALKENES; ANISOLES; ANTINEOPLASTIC AGENTS; BIOLOGICAL PRODUCTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; HYDROGENATION; SESQUITERPENES; STEREOISOMERISM;

EID: 64149089841     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9000405     Document Type: Article

References (46)

1. Bohlmann, F.; Zdero, C.; Le Van, N. Phytochemistry 1979, 18, 99.
2. Ho, T.-L.; Lee, K.-Y.; Chen, C.-K. J. Org. Chem. 1997, 62, 3365.
3. For a review, see Nicolaou, K. C.; Snyder, S. A. Angew. Chem., Int. Ed. 2005, 44, 1012.
4. For reviews concerning ring contraction reactions, see: (a) Redmore, D.; Gutsche, C. D. In AdVances in Alicyclic Chemistry; Hart, H., Karabastos, G. J., Eds.; Academic Press: New York, London, 1971; Vol. 3, p 1.
5. (b) Silva, L. F., Jr. Tetrahedron 2002, 58, 9137. For a review concerning ring contraction reactions mediated by iodine(III), see:
6. (c) Silva, L. F., Jr. Molecules 2006, 11, 421. For reviews concerning ring contraction reactions mediated by thallium (III), see:
7. (d) Ferraz, H. M. C.; Silva, L. F., Jr. Quim. NoVa 2000, 23, 216.
8. (a) Ferraz, H. M. C.; Silva, L. F., Jr.; Vieira, T. O. Tetrahedron 2001, 57, 1709.
9. (b) Ferraz, H. M. C.; Silva, L. F., Jr. Tetrahedron 2001, 57, 9939.
10. (c) Ferraz, H. M. C.; Aguilar, A. M.; Silva, L. F., Jr. Synthesis 2003, 7, 1031.
11. (d) Ferraz, H. M. C.; Aguilar, A. M.; Silva, L. F., Jr. Tetrahedron 2003, 59, 5817.
12. (e) Silva, L. F., Jr.; Sousa, R. M. F.; Ferraz, H. M. C.; Aguilar, A. M. J. Braz. Chem. Soc. 2005, 16, 1160.
13. (f) Silva, L. F., Jr.; Quintiliano, S. A. P.; Craveiro, M. V.; Vieira, F. Y. M.; Ferraz, H. M. C. Synthesis 2007, 355.
14. (g) Silva, L. F., Jr.; Craveiro, M. V. Org. Lett. 2008, 10, 5417.
15. (h) Ferraz, H.; M, C.; Carneiro, V. M. T.; Silva, L. F., Jr. Synthesis 2009, 385.
16. Silva, L. F., Jr.; Siqueira, F. A.; Pedrozo, E. C.; Vieira, F. Y. M.; Doriguetto, A. C. Org. Lett. 2007, 9, 1433.
17. (a) This theme was discussed in the editorial of the JACS virtual issue regarding the total synthesis of natural products: Roush, W. R. J. Am. Chem. Soc. 2008, 130, 6654.
18. (b) See also: Hudlicky, T.; Reed, J. W. The Way of Synthesis; Wiley-VCH: Germany, 2007.
19. For broad reviews, see: (a) Maimone, T. J.; Baran, P. S. Nat. Chem. Biol. 2007, 3, 396.
20. (b) Wilson, R. M.; Danishefsky, S. J. J. Org. Chem. 2006, 71, 8329.
21. (c) Newman, D. J.; Cragg, G. M. J. Nat. Prod 2007, 70, 461. For selected articles and reviews concerning the total synthesis and the biological evaluation of natural products, see:
22. (d) Fennell, K. A.; Möllmann, U.; Miller, M. J. J. Org. Chem. 2008, 73, 1018.
23. (e) Bonazzi, S.; Guttinger, S.; Zemp, I.; Kutay, U.; Gademann, K. Angew. Chem., Int. Ed. 2007, 46, 8707.
24. (f) Adrio, J.; Cuevas, C.; Manzanares, I.; Joullié, M. M. J. Org. Chem. 2007, 72, 5129.
25. (g) Nicolaou, K. C.; Wu, T. R.; Sarlah, D.; Shaw, D. M.; Rowcliffe, E.; Burton, D. R. J. Am. Chem. Soc. 2008, 130, 11114.
26. (h) Bowers, A.; West, N.; Taunton, J.; Schreiber, S. L.; Bradner, J. E.; Williams, R. M. J. Am. Chem. Soc. 2008, 130, 11219.
27. (i) Tichenor, M. S.; Boger, D. L. Nat. Prod. Rep. 2008, 25, 220.
28. (j) Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M. Angew. Chem., Int. Ed. 2008, 47, 2365.
29. For a review, see: Wilson, R. M.; Danishefsky, S. J. Chem. Soc. Rev. 2007, 36, 1207.
30. For reviews regarding asymmetric hydrogenation mediated by iridium catalysts, see: (a) Roseblade, S. J.; Pfaltz, A. Acc. Chem. Res. 2007, 70, 1402.
31. (b) Källström, K.; Munslow, I.; Andersson, P. G. Chem. Eur. J. 2006, 12, 3194.
32. (c) Pfaltz, A.; Blankenstein, J.; Hilgraf, R.; Hormann, E.; McIntyre, S.; Menges, F.; Schonleber, M.; Smidt, S. P.; Wustenberg, B.; Zimmermann, N. Adv. Synth. Catal. 2003, 345, 33. See also ref 13.
33. For recent developments in asymmetric hydrogenation, see: Special Issue on Hydrogenation and Transfer Hydrogenation, Acc. Chem. Res. 2007, 70 (12).
34. Zubaidha, P. K.; Chavan, S. P.; Racherle, U. S.; Ayyangar, N. R. Tetrahedron 1991, 47, 5759.
35. For a review regarding asymmetric hydrogenation of non-functionalized olefins, see: Cui, X.; Burgess, K. Chem. Rev. 2005, 105, 3272.
36. (a) Lightfoot, A.; Schnider, P.; Pfaltz, A. Angew. Chem., Int. Ed. 1998, 37, 2897.
37. (b) Menges, F.; Pfaltz, A. AdV. Synth. Catal. 2002, 344, 40.
38. (ba) Smidt, S. P.; Menges, F.; Pfaltz, A. Org. Lett. 2004, 6, 2023.
39. (c) Kaiser, S.; Smidt, S. P.; Pfaltz, A. Angew. Chem., Int. Ed. 2006, 45, 5194.
40. (d) Schrems, M. G.; Neumann, E.; Pfaltz, A. Heterocycles 2008, 76, 771.
41. Schrems, M. G.; Neumann, E.; Pfaltz, A. Angew. Chem., Int. Ed. 2007, 46, 8274.
42. Chavan, S. P.; Thakkar, M.; Kalkote, U. R. Tetrahedron Lett. 2007, 48, 643.
43. Fagerlund, U. H. M.; Idler, D. R. J. Am. Chem, Soc. 1957, 79, 6473.
44. Hauser, F. M.: Prasanna, S. Synthesis 1980, 621.
45. Schow, S. R.; Bloom, J. D.; Thompson, A. S.; Winzenberg. K. N.; Smith, A. B., III. J. Chem. Soc. 1986, 108, 2662.
46. Bell, A. A.; Stipanovic, R. D.; Zhang. J.; Mace, M. E. Photochemistry 1998, 49, 431.