Total synthesis of (+)-neomarinone

Chemistry - A European Journal

Volumn 15, Issue 4, 2009, Pages 910-916

  Peña López, Miguel ^a   Martínez, M Montserrat ^a   Sarandeses, Luis A ^a   Sestelo, José Pérez ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

Alkylations; Asymmetric synthesis; Cuprate additions; Diels Alder reaction; Natural products

Indexed keywords

ALKYLATION; CHEMICAL REACTIONS; COPPER COMPOUNDS; ELECTRON TRANSITIONS; HYDROCARBONS; STEREOCHEMISTRY;

ALKYLATIONS; ASYMMETRIC SYNTHESIS; CUPRATE ADDITIONS; DIELS-ALDER REACTION; NATURAL PRODUCTS;

ADDITION REACTIONS;

NAPHTHOQUINONE; NEOMARINONE;

ALKYLATION; ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; NAPHTHOQUINONES; STEREOISOMERISM;

EID: 58449124628     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802021     Document Type: Article

References (40)

1. I. H. Hardt, P. R. Jensen, W. Fenical, Tetrahedron Lett. 2000, 41, 2073-2076.
2. T.J. Simpson, Top. Curr. Chem. 1998, 195, 1-48.
3. a) M. Ishibashi, S. Funayama, Y. Anraku. K. Komiyama, S. Omura, J. Antibiot. 1991, 44, 390-395;
4. b) S. Funayama. M. Ishibashi, K. Komiyama, S. Omura, J. Org. Chem. 1990, 55, 1132-1133.
5. C. Pathirana, P. R. Jensen, W. Fenical, Tetrahedron Lett. 1992, 33, 7663-7666.
6. T. Kuzuyama, H. Seto, Nat. Prod. Rep. 2003, 20, 171-183.
7. J. A. Kalailzis, Y. Hamano, G. Nilsen, B. S. Moore, Org. Lett. 2003, 5, 4449-4452.
8. R. J. Capon, D. J. Faulkner, J. Am. Chem. Soc. 1984, 106, 1819-1822.
9. J. Carroll. E. N. Jonsson, R. Ebel, M. S. Hartman, T. R. Holman, P. Crews. J. Org. Chem. 2001, 66, 6847-6851.
10. a) A. B. Smith, J. Pérez Sestelo, P. G. Dormer, J. Am. Chem. Soc. 1995, 117, 10755-10756:
11. b) A. B. Smith, J. Pérez Sestelo. P. G. Dormer, Heterocycles 2000, 52, 1315-1328.
12. a) M. E. Botha, R. G. F. Giles, S. C. Yorke, J. Chem. Soc. Perkin Trans. 1 1991, 85-88;
13. b) M. Blouin, M. C. Béland, P. Brassard, J. Org. Chem. 1990, 55, 1466-1471.
14. a) J. Pérez Sestelo, M. M. Real, L. A. Sarandeses, Tetrahedron Lett. 1999, 40, 985-988:
15. b) J. Pérez Sestelo, M. M. Real, L. A. Sarandeses, J. Org. Chem. 2001, 66, 1395-1402.
16. J. A. Marshall, X. Sniping, J. Org. Chem. 1995, 60, 7230-7237.
17. a) W. Lehnert, Tetrahedron 1972, 28, 663-666;
18. b) D. Courtheyn, R. Verhé, N. De Kimpe, L. De Buyck. N. Schamp, J. Org. Chem. 1981, 46, 3226-3229.
19. The Z and E configuration was determined by J-HMBC experiments.
20. a) H. J. Reich, S. Wollowitz. Org. React. 1993, 44, 1-296;
21. b) H. J. Reich. J. M. Renga, I. L. Reich, J. Am. Chem. Soc. 1975, 97, 5434-5447.
22. As the enone showed low stability at RT, it was kept at -20°C and used immediately after its preparation.
23. a) X. Cuesta, A. González. J. Bonjoch. Tetrahedron: Asymmetry 1999, 10, 3365-3370;
24. b) I. G. Guest. C. R. Hugues. R. Ramage. A. Sattar, J. Chem. Soc. Chem. Commun. 1973, 526-527.
25. CCDC 703928 contains the supplementary crystallography data for this paper. These data can be obtained free of charge from The Cambridge Crystallography Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
26. a) W. J. Scott, J. E. McMurry, Acc. Chem. Res. 1988, 21, 47-54;
27. b) K. Ritter, Synthesis 1993, 735-762.
28. a) I. Pérez, J. Pérez Sestelo, L. A. Sarandeses, Org. Lett. 1999, 1, 1267-1269;
29. b) I. Pérez, J. Pérez Sestelo, L. A. Sarandeses, J. Am. Chem. Soc. 2001, 123, 4155-4160.
30. For a synthesis of the racemic iodide 5 see: R. M. Suárez. M. M. Martínez. L. A. Sarandeses. J. Pérez Sestelo, Tetrahedron Lett. 2007, 48, 6493-6495.
31. a) K. C. Nicolaou, G. Vassilikogiannakis, W. Mägerlein, R. Kranich, Chem. Eur. J. 2001. 7, 5359-5370;
32. b) A. A. Boezio. E. R. Jarvo, B. M. Lawrence, E. N. Jacobsen. Angew. Chem. 2005, 117, 6200-6204;
33. Angew. Chem. Int. Ed. 2005, 44, 6046-6050.
34. a) C. L. Chai, J. A. Elix, F. K. Moore, J. Org. Chem. 2006, 71, 992-1001;
35. b) C. S. P. McErlean. C. J. Moody, J. Org. Chem. 2007, 72, 10298-10301;
36. c) P. Stahl, L. Kissau, R. Mazitschek, A. Huwe, P. Furet, A. Giannis, H. Waldmann, J. Am. Chem. Soc 2001, 123, 11586-11593;
37. d) M. C. Pirrung, Z. Li, K. Park, J. Zhu, J. Org. Chem. 2002, 67, 7919-7926.
38. a) T. Ling, E. Poupon, E. J. Rueden, E. A. Theodorakis. Org. Lett. 2002, 4, 819-822;
39. b) S. Poigny, M. Guyot, M. Samadi, Tetrahedron 1998, 54, 14791-14802.
40. H. Arimoto, D. Uemura in Quaternary Stereocenters, (Eds.: J. Christoffers, A. Baro), Wiley-VCH, Weinheim, 2005. Chapter 1, pp. 1-24.