General access to taiwaniaquinoids based on a hypothetical abietane C7-C8 cleavage biogenetic pathway

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 573-584

  Tapia, Rubén ^a   Guardia, Juan J ^a   Alvarez, Esteban ^a   Haidöur, Ali ^a   Ramos, Jose M ^a   Alvarez Manzaneda, Ramón ^b   Chahboun, Rachid ^a   Alvarez Manzaneda, Enrique ^a  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF ALMERÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

A-CARBON; BIOGENETIC PATHWAYS; BIOLOGICAL ACTIVITIES; BIOSYNTHETIC PATHWAY; DITERPENES; DOUBLE BONDS; NEW STRATEGY; TERPENOIDS;

CHEMISTRY;

ORGANIC COMPOUNDS;

ABIETANE DERIVATIVE; ABIETIC ACID; BENZILIC ACID; CYCLOPENTANE; TAIWANIAQUINOID DERIVATIVE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; NUCLEOPHILICITY; PINACOL REARRANGEMENT; SYNTHESIS;

DITERPENES; DITERPENES, ABIETANE; MOLECULAR STRUCTURE; STEREOISOMERISM; TERPENES;

EID: 84855540091     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202163y     Document Type: Article

References (50)

1. For a recent review, see: Majetich, G.; Shimkus, J. M. J. Nat. Prod. 2010, 73, 284-298
2. Lin, W.; Fang, J.; Cheng, Y. Phytochemistry 1996, 42, 1657-1663
3. Chang, C.-I.; Chang, J.-Y.; Kuo, C.-C.; Pan, W.-Y.; Kuo, Y.-H. Planta Med. 2005, 71, 72-76
4. Kawazoe, K.; Yamamoto, M.; Takaishi, Y.; Honda, G.; Fujita, T.; Sezik, E.; Yesilada, E. Phytochemistry 1999, 50, 493-497
5. Lin, W.; Fang, J.; Cheng, Y. Phytochemistry 1995, 40, 871-873
6. Chang, C.; Chien, S.; Lee, S.; Kuo, Y. Chem. Pharm. Bull. 2003, 51, 1420-1422
7. Ohtsu, H.; Iwamoto, M.; Ohishi, U.; Matsunaga, S.; Tanaka, R. Tetrahedron Lett. 1999, 40, 6419-6422
8. Iwamoto, M.; Ohtsu, H.; Tokuda, H.; Nishino, H.; Matsunaga, S.; Tanaka, R. Bioorg. Med. Chem. 2001, 9, 1911-1921
9. Minami, T.; Iwamoto, M.; Ohtsu, H.; Ohishi, H.; Tanaka, R.; Yoshitake, A. Planta Med. 2002, 68, 742-745
10. Hanson, J. Nat. Prod. Rep. 2004, 21, 312-320
11. This classification of the different synthetic approaches has been utilized for some polycyclic terpenoids. See: Kawada, K.; Kim, M.; Watt, D. S. Org. Prep. Proced. Int. 1989, 21, 521-618
12. McFadden, R. M.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 7738-7739
13. Fillion, E.; Fishlock, D. J. Am. Chem. Soc. 2005, 127, 13144-13145
14. Li, S.; Chiu, P. Tetrahedron Lett. 2008, 49, 1741-1744
15. Planas, L.; Mogi, M.; Takita, H.; Kajimoto, T.; Node, M. J. Org. Chem. 2006, 71, 2896-2898
16. Banerjee, M.; Mukhopadhyay, R.; Achari, B.; Banerjee, A. K. Org. Lett. 2003, 5, 3931-3933
17. J. Org. Chem. 2006, 71, 2787-2796.
18. Liang, G.; Xu, Y.; Seiple, I. B.; Trauner, D. J. Am. Chem. Soc. 2006, 128, 11022-11023
19. Tang, S.; Xu, Y.; He, J.; He, Y.; Zheng, J.; Pan, X.; She, X. Org. Lett. 2008, 10, 1855-1858
20. Alvarez-Manzaneda, E.; Chahboun, R.; Cabrera, E.; Alvarez, E.; Alvarez-Manzaneda, R.; Meneses, R.; Es-Samti, H.; Fernández, A. J. Org. Chem. 2009, 74, 3384-3388
21. Liao, X.; Stanley, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 2088-2091
22. Jana, C. K.; Scopelliti, R.; Gademann, K. Chem.-Eur. J. 2010, 16, 7692-7695
23. Katoh, T.; Akagi, T.; Noguchi, C.; Kajimoto, T.; Node, M.; Tanaka, R.; Nishizawa, M.; Ohtsu, H.; Suzuki, N.; Saito, K. Bioorg. Med. Chem. 2007, 15, 2736-2748
24. Alvarez-Manzaneda, E.; Chahboun, R.; Cabrera, E.; Alvarez, E.; Haidour, A.; Ramos, J. M.; Alvarez-Manzaneda, R.; Hmamouchi, M.; Es-Samti, H. Chem. Commun. 2009, 592-594
25. Alvarez-Manzaneda, E.; Chahboun, R.; Cabrera, E.; Alvarez, E.; Haidour, A.; Ramos, J. M.; Alvarez-Manzaneda, R.; Charrah, Y.; Es-Samti, H. Org. Biomol. Chem. 2009, 7, 5146-5155
26. Li, A.; She, X.; Zhang, J.; Wu, T.; Pan, X. Tetrahedron 2003, 59, 5737-5741
27. 4 in the presence of AD-mix (β) gave a hydroxy diketone. See: Jana, C. K.; Scopelliti, R.; Gademann, K. Synthesis 2010, 2223-2232
28. Alvarez-Manzaneda, E.; Chahboun, R.; Bentaleb, F.; Alvarez, E.; Escobar, M. A.; Sad-Diki, S.; Cano, M. J.; Messouri, I. Tetrahedron 2007, 63, 11204-11212
29. Duc, D. K. M.; Fetizon, M.; Lazare, S. J. Chem. Soc., Chem. Commun. 1975, 282
30. Duc, D. K. M.; Fetizon, M.; Flament, J. P. J. Chem. Soc., Chem. Commun. 1972, 886-887
31. Duc, D. K. M.; Fetizon, M.; Flament, J. P. Tetrahedron 1975, 31, 1897-1902
32. Duc, D. K. M.; Fetizon, M.; Kone, M. Tetrahedron 1975, 31, 1903-1905
33. Weibel, J.-M.; Heissler, D. Tetrahedron Lett. 1994, 35, 473-476
34. Katsumura, S.; Kimura, A.; Isoe, S. Tetrahedron 1989, 45, 1337-1346
35. White, G. D.; Skeean, R. W.; Trammell, G. L. J. Org. Chem. 1985, 50, 1939-1948
36. Miyake, T.; Kigoshi, H.; Akita, H. Tetrahedron: Asymmetry 2007, 18, 2915-2922
37. Ishihara, K.; Ishibashi, H.; Yamamoto, H. J. Am. Chem. Soc. 2001, 123, 1505-1506
38. Alvarez-Manzaneda, E.; Chahboun, R.; Alvarez, E.; Tapia, R.; Alvarez-Manzaneda, R. Chem. Commun. 2010, 46, 9244-9246
39. Morita, S.; Yatagai, M.; Fujita, S. Mokuzai Gakkaishi 1995, 41, 938-944
40. De Pascual Teresa, J.; Barrero, A. F.; Caballero, M. C.; San Feliciano, A. An. Quim. 1978, 74, 966-971
41. Ribo, J. M.; Raventos, J. U.; Serra, A. M. Phytochemistry 1977, 16, 767
42. Norin, T.; Winell, B. Phytochemistry 1971, 10, 2818-2821
43. Chen, X.; Ding, J.; Ye, Y.-M.; Zhang, J.-S. J. Nat. Prod. 2002, 65, 1016-1020 and references cited therein
44. Anderson, J. C.; Davies, E. A. Tetrahedron 2010, 66, 6300-6308
45. Ichikawa, J.; Lapointe, G.; Iwai, Y. Chem. Commun. 2007, 2698-2700
46. Nadano, R.; Iwai, Y.; Mori, T.; Ichikawa, J. J. Org. Chem. 2006, 71, 8748-8754
47. Berry, M. B.; Rowlands, G. J.; Craig, D.; Jones, P. S. Chem. Commun. 1997, 2141-2142
48. Jones, A. D.; Knight, D. W. Chem. Commun. 1996, 915-916
49. Trost, M. B.; Bonk, P. J. J. Am. Chem. Soc. 1985, 107, 1778-1781
50. Yoshikawa, K.; Suzuki, K.; Umeyama, A.; Arihara, S. Chem. Pharm. Bull. 2006, 54, 574-578