A direct synthesis of 1,7-dioxaspiro[4.5]decanes from the new 3-methylidenepentane-1,5-dianion synthon

Tetrahedron

Volumn 62, Issue 10, 2006, Pages 2264-2277

  Alonso, Francisco ^a   Meléndez, Jaisiel ^a   Soler, Tatiana ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Dianion synthon; DTBB catalysed lithiation; Intermolecular hydrogen bonding; Spirocyclic ethers

Indexed keywords

3 METHYLIDENEPENTANE 1,5 DIANION; 4 PHENYLSULFANYL 2 (2 PHENYLSULFANYLETHYL)BUT 1 ENE; ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; DECANE; LACTONE; LITHIUM; SILVER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; ETHERIFICATION; HYDROLYSIS; MOLECULAR BIOLOGY; OXIDATION; POWDER; PRIORITY JOURNAL; TEMPERATURE;

EID: 32444448855     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.12.008     Document Type: Article

References (61)

1. See, for instance: (a) G.E. Keck, and A. Palani Tetrahedron Lett. 34 1993 3223 3224
2. C.-J. Li Tetrahedron Lett. 36 1995 517 518
3. A. Krief, and W. Dumont Tetrahedron Lett. 38 1997 657 660
4. K.-T. Kang, E.H. Kim, W.J. Kim, N.S. Song, J.K. Shin, and B.Y. Cho Synlett 1998 921 923
5. A. Krief, W. Dumont, I.E. Markó, F. Murphy, J.-C. Vanherck, R. Duval, T. Ollevier, and U. Abel Synlett 1998 1219 1222
6. A. Takuwa, H. Saito, and Y. Nishigaichi Chem. Commun. 1999 1963 1964
7. A.G.M. Barrett, D.C. Braddock, P.D. de Koning, A.J.P. White, and D.J. Williams J. Org. Chem. 65 2000 375 380
8. C.-M. Yu, J.-Y. Lee, B. So, and J. Hong Angew. Chem., Int. Ed. 41 2002 161 163
9. T.W. Lee, J.A. Channon, C. Cregg, J.R. Porter, F.S. Roden, and H.T.-L. Yeoh Tetrahedron 45 1989 5877 5886
10. I. Manteca, B. Etxarri, A. Ardeo, S. Arrasate, I. Osante, N. Sotomayor, and E. Lete Tetrahedron 54 1998 12361 12378
11. See, for instance: (a) M.K. Ticku, T.P. Burch, and W. Davis Adv. Biochem. Phsychopharmacol. 29 1981 411 419
12. G.R. Pettit, G.M. Cragg, M.I. Suffness, D. Gust, F.E. Boettner, M. Williams, J.A. Saenz-Renauld, P. Brown, and J.M. Schmidt J. Org. Chem. 49 1984 4258 4266
13. Y. Uosaki, S.Z. Kawada, N. Nakano, Y. Saitoh, and H. Sano J. Antibiot. 46 1993 235 240
14. J.E. McCullough, M.T. Muller, A.J. Howells, A. Maxwell, J. O'Sullivan, R.S. Summerill, W.L. Parker, J.S. Wells, D.P. Bonner, and P.B. Fernandes J. Antibiot. 46 1993 526 530
15. S. Kawada, Y. Yamashita, K. Ochiai, K. Ando, T. Iwasaki, T. Takiguchi, and H. Nakano J. Antibiot. 48 1995 211 216
16. M. Binaschi, G. Zagotto, M. Palumbo, F. Zunino, R. Farinosi, and G. Capranico Cancer Res. 57 1997 1710 1716
17. For a review, see: H.N.C. Wong Eur. J. Org. Chem. 1999 1757 1765
18. See, for instance: (a) J. Eames, M.A. de las Heras, R.V.H. Jones, and S. Warren Tetrahedron Lett. 37 1996 4581 4584
19. L. Caggiano, D.J. Fox, D. House, Z.A. Jones, F. Kerr, and S.W. Warren J. Chem. Soc., Perkin Trans. 1 2002 2634 2645
20. L. Han, T. Hatano, T. Yoshida, and T. Okuda Chem. Pharm. Bull. 42 1994 1399 1409
21. R.-S. Xu, Y.-J. Lu, and J.-H. Chu Tetrahedron 38 1982 2667 2670
22. See, for instance: (a) W.-M. Wu, and Y.-L. Wu J. Chem. Soc., Perkin Trans. 1 2000 4279 4283
23. D.-Y. Wang, Y.-L. Wu, Y. Wu, J. Liang, and Y. Li J. Chem. Soc., Perkin Trans. 1 2001 605 609
24. S. Hindley, S.A. Ward, R.C. Storr, N.L. Searle, P.G. Bray, B.K. Park, J. Davies, and P.M. O'Neill J. Med. Chem. 45 2002 1052 1063
25. (a) Sundelin, K. G. R.; Powell, J. E.; Kollmeyer, W. D. U.S. Patent 4,410,354, 1983; Chem. Abstr. 1984, 100, 103178.
26. (b) Pilgram, K. H. U.S. Patent 4,602,933, 1986; Chem. Abstr. 1986, 105, 220999.
27. (c) Pilgram, K. H., DE Patent 3712464, 1987; Chem. Abstr. 1988, 108, 55881.
28. R. Csuk, A. Fürstner, H. Sterk, and H. Weidmann J. Carbohydr. Chem. 5 1986 459 467
29. B. Werschkun, and J. Thiem Tetrahedron: Asymmetry 16 2005 569 576
30. D.J. Holt, W.D. Barker, P.R. Jenkins, D.L. Davies, S. Garratt, J. Fawcett, D.R. Russell, and S. Ghosh Angew. Chem., Int. Ed. 37 1998 3298 3300
31. D.J. Holt, W.D. Barker, and P.R. Jenkins J. Org. Chem. 65 2000 482 493
32. B. Schmidt, and M. Westhus Tetrahedron 56 2000 2421 2426
33. D.J. Wallace, P.G. Bulger, D.J. Kennedy, M.S. Ashwood, I.F. Cottrell, and U.-H. Dolling Synlett 2001 357 360
34. B. Schmidt, B. Costisella, R. Roggenbuck, M. Westhus, H. Wildemann, and P. Eilbracht J. Org. Chem. 66 2001 7658 7665
35. H. Marschall, J. Penninger, and P. Weyerstahl Liebigs Ann. Chem. 1982 49 67
36. M. Yus Chem. Soc. Rev. 25 1996 155 161
37. D.J. Ramón, and M. Yus Eur. J. Org. Chem. 2000 225 237
38. M. Yus Synlett 2001 1197 1205
39. M. Yus Z. Rappoport I. Marek The Chemistry of Organolithium Compounds Vol. 1 2004 Wiley Chichester 647 747
40. F. Alonso, E. Lorenzo, and M. Yus Tetrahedron Lett. 38 1997 2187 2190
41. F. Alonso, E. Lorenzo, and M. Yus Tetrahedron Lett. 39 1998 3303 3306
42. E. Lorenzo, F. Alonso, and M. Yus Tetrahedron Lett. 41 2000 1661 1665
43. E. Lorenzo, F. Alonso, and M. Yus Tetrahedron 56 2000 1745 1757
44. F. Alonso, E. Lorenzo, J. Meléndez, and M. Yus Tetrahedron 59 2003 5199 5208
45. F. Alonso, L.R. Falvello, P.E. Fanwick, E. Lorenzo, and M. Yus Synthesis 2000 949 952
46. F. Alonso, J. Meléndez, and M. Yus Helv. Chim. Acta 85 2002 3262 3271
47. F. Alonso, J. Meléndez, and M. Yus Tetrahedron Lett. 45 2004 1717 1720
48. F. Alonso, B. Dacunha, J. Meléndez, and M. Yus Tetrahedron 61 2005 3437 3450
49. F. Alonso, J. Meléndez, and M. Yus Tetrahedron Lett. 46 2005 6519 6524
50. E.J. Corey, and D. Seebach J. Org. Chem. 31 1966 4097 4099
51. E.J. Corey, and M. Jautelat Tetrahedron Lett. 55 1968 5787 5788
52. C. Blomberg The Barbier Reaction and Related Processes 1993 Springer Berlin
53. F. Alonso, and M. Yus Recent Res. Dev. Org. Chem. 1 1997 397 436
54. N.S. Bhacca, and D.H. Williams Applications of NMR Spectroscopy in Organic Chemistry 1964 Holden-Day San Francisco pp 116-117
55. W.F. Berkowitz, J. Perumattam, and A. Amarasekara J. Org. Chem. 52 1987 1119 1124
56. G. Balavoine, C. Eskenazi, and F. Meuier J. Mol. Catal. 30 1985 125 133
57. Parsons, S.; Gould, B. ROTAX, version 26th November; University of Edimburgh, with additions by Richard Cooper (Oxford) and Louis Farrugia (Glasgow), 2001.
58. SAINT: Area Detector Integration Software, version 6.28A; Siemens Industrial Automation Inc.: Madison, WI, 1995.
59. Sheldrick, G. M. SADABS: Area Detector Absorption Correction; Göttingen University: Göttingen, Germany, 1996.
60. SIR92: Altomare, A.; Cascarano, G.; Giacovazzo, G.; Guagliardi, A., J. Appl. Crystallogr. 1993, 26, 343-350.
61. Sheldrick, G. M. SHELX97 [Includes SHELXS97, SHELXL97 and CIFTAB]-Programs for Crystal Structure Analysis (Release 97-2). Institüt für Anorganische Chemie der Universität: Tammanstrasse 4, 37073 Göttingen, Germany, 1998.