Synthesis of (±)-aureol by bioinspired rearrangements

Journal of Organic Chemistry

Volumn 80, Issue 3, 2015, Pages 1866-1870

  Rosales, Antonio ^b   Muñoz Bascón, Juan ^a   Roldan Molina, Esther ^a   Rivas Bascón, Nazaret ^a   Padial, Natalia M ^a   Rodríguez Maecker, Roman ^d   Rodríguez García, Ignacio ^c   Oltra, J Enrique ^a  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF SEVILLE   (Spain)

^c UNIVERSITY OF ALMERÍA   (Spain)

^d UNIVERSIDAD DE LAS FUERZAS ARMADAS ESPE   (Ecuador)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS;

CASCADE CYCLIZATION; TITANOCENES;

CYCLIZATION;

AUREOL; BIOMIMETIC MATERIAL; EPOXIDE; FARNESOL; METHYL GROUP; SESQUITERPENOID; TITANOCENE; UNCLASSIFIED DRUG; ORGANOMETALLIC COMPOUND; SESQUITERPENE;

ARTICLE; BIOLOGICAL ACTIVITY; BIOMIMETICS; CATALYST; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ORGANIC CHEMISTRY; RADICAL REACTION; BIOCHEMISTRY; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BIOCHEMICAL PROCESSES; CATALYSIS; CYCLIZATION; EPOXY COMPOUNDS; FARNESOL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SESQUITERPENES; STEREOISOMERISM;

EID: 84922705950     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502841u     Document Type: Article

References (29)

1. Capon, R. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: New York, 1995; Vol. 15, p 89.
2. Djura, P.; Stierle, D. B.; Sullivan, B.; Faulkner, D. J.; Arnold, E.; Clardy, J. J. Org. Chem. 1980, 45, 1435
3. Ciminiello, P.; Dell'Aversano, C.; Fattorusso, E.; Magno, S.; Pansini, M. J. Nat. Prod. 2000, 63, 263
4. Minagawa, K.; Kouzuki, S.; Kamigauchi, T. J. Antibiot. 2002, 55, 165 and references cited therein
5. Wright, A. E.; Rueth, S. A.; Cross, S. S. J. Nat. Prod. 1991, 54, 1108
6. Longley, R. E.; McConnell, O. J.; Essich, E.; Harmody, D. J. Nat. Prod. 1993, 56, 915
7. Wright, A. E.; Cross, S. S.; Burres, N. S.; Koehn, F. (Harbor Branch Oceanographics Institution, Inc., Fort Pierce, FL). PCT WO 9112250 A1, August 22, 1991.
8. Sakurai, J.; Oguchi, T.; Watanabe, K.; Abe, H.; Kanno, S.; Ishikawa, M.; Katoh, T. Chem.-Eur. J. 2008, 14, 829 and references cited therein
9. Marcos, I. S.; Conde, A.; Moro, R. F.; Basabe, P.; Diez, D.; Urones, J. G. Tetrahedron 2010, 66, 8280
10. Taishi, T.; Takechi, S.; Mori, S. Tetrahedron Lett. 1998, 39, 4347
11. Sakurai, J.; Kikudhi, T.; Takahasi, O.; Watanabe, K.; Katoh, T. Eur. J. Org. Chem. 2011, 2948
12. Watanabe, K.; Sakurai, J.; Abe, H.; Katoh, T. Chem. Commun. 2010, 46, 4055
13. Ngoc, D. T.; Albicker, M.; Schneider, L.; Cramer, N. Org. Biomol. Chem. 2010, 8, 1781
14. Kuan, K. K. W.; Pepper, H. P.; Bloch, W. M.; George, J. H. Org. Lett. 2012, 14, 4710
15. Barrero, A. F.; Oltra, J. E.; Cuerva, J. M.; Rosales, A. J. Org. Chem. 2002, 67, 2566
16. Barrero, A. F.; Rosales, A.; Cuerva, J. M.; Oltra, J. E. Org. Lett. 2003, 5, 1935
17. Justicia, J.; Rosales, A.; Buñuel, E.; Oller-López, J. L.; Valdivia, M.; Haïdour, A.; Oltra, J. E.; Barrero, A. F.; Cárdenas, D. J.; Cuerva, J. M. Chem.-Eur. J. 2004, 10, 1778
18. Justicia, J.; álvarez de Cienfuegos, L.; Estévez, R. E.; Paradas, M.; Lasanta, A. M.; Oller, J. L.; Rosales, A.; Cuerva, J. M.; Oltra, J. E. Tetrahedron 2008, 64, 11938
19. Justicia, J.; álvarez de Cienfuegos, L.; Campaña, A. G.; Miguel, D.; Jakoby, V.; Gansäuer, A.; Cuerva, J. M. Chem. Soc. Rev. 2011, 40, 3525
20. Gansäuer, A.; Rosales, A.; Justicia, J. Synlett 2006, 6, 927
21. Gansäuer, A.; Justicia, J.; Rosales, A.; Worgull, D.; Rinker, B.; Cuerva, J. M.; Oltra, J. E. Eur. J. Org. Chem. 2006, 4115
22. Rosales, A.; López-Sánchez, C.; álvarez-Corral, M.; Muñoz-Dorado, M.; Rodríguez-García, I. Lett. Org. Chem. 2007, 4, 553
23. Rosales, A.; Muñoz-Bascón, J.; Morales-Alcázar, V. M.; Castilla, J. A.; Oltra, J. E. RSC Adv. 2012, 2, 12922
24. Snyder, S. A.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 740
25. Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1995.
26. Zard, S. Z. In Radical in Organic Synthesis; Renaud, P.; Mukund, P. S.; Renaud, P.; Mukund, P. S., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 1, p 90.
27. Urban, S.; Capon, R. J. Aust. J. Chem. 1994, 47, 1023
28. Oblak, E. Z.; VanHyst, M. D.; Li, J.; Wiemer, A. J.; Wright, D. L. J. Am. Chem. Soc. 2014, 136, 4309
29. Colombo, L.; Gennari, C.; Potenza, D.; Scolastico, C.; Aragozzini, F.; Gualandris, R. J. Chem. Soc., Perkin Trans. 1 1982, 2, 365