Iridium-catalyzed oxidative lactonization and intramolecular Tishchenko reaction of δ-ketoaldehydes for the synthesis of isocoumarins and 3,4-dihydroisocoumarins

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 10, 2005, Pages 2583-2585

  Suzuki, Takeyuki ^a   Yamada, Taichiro ^a   Watanabe, Kazuhiro ^a   Katoh, Tadashi ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Intramolecular Tischenko reaction; Iridium catalyst; Isocoumarin; Ketoaldehyde; Oxidative lactonization

Indexed keywords

ALDEHYDE DERIVATIVE; IRIDIUM; ISOCOUMARIN DERIVATIVE; LIGAND;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION; DRUG SYNTHESIS; LACTONIZATION; MOLECULE; OXIDATION; QUANTUM YIELD; ROOM TEMPERATURE;

EID: 18244376108     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.03.043     Document Type: Article

References (49)

1. R.D. Barry Chem. Rev. 64 1964 229
2. J.D. Hepworth, C.D. Gabbutt, and B.M. Heron A. McKillop Comprehensive Heterocyclic Chemistry II 5 1996 Pergamon Oxford 436 438
3. E. Napolitano Org. Prep. Proced. Int. 29 1997 631
4. C.N. Lewis, P.L. Spargo, and J. Staunton Synthesis 1986 944
5. T. Yao, and R.C.J. Larock Org. Chem. 68 2003 5936 and references therein
6. R.C. Larock, S. Varaprath, H.H. Lau, and C.A. Fellows J. Am. Chem. Soc. 106 1984 5274
7. F.M. Hauser, and V.M. Baghdanov J. Org. Chem. 53 1988 4676
8. I. Shimoyama, Y. Zhang, G. Wu, and E. Negishi Tetrahedron Lett. 31 1990 2841
9. N.G. Kundu, M. Pal, and B. Nandi J. Chem. Soc., Perkin Trans. 1 1998 561
10. M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, and M. Nomura J. Org. Chem. 63 1998 5211
11. L. Wang, and W. Shen Tetrahedron Lett. 39 1998 7625
12. H. Sashida, and A. Kawamukai Synthesis 1999 1145
13. R.C. Larock, M.J. Doty, and X. Han J. Org. Chem. 64 1999 8770
14. Y. Ogawa, M. Maruno, and T. Wakamatsu Heterocycles 41 1995 2587
15. F. Bellina, D. Ciucci, P. Vergamini, and R. Rossi Tetrahedron 56 2000 2533
16. N. Menashe, and Y. Shvo J. Org. Chem. 58 1993 7434
17. E. Negishi, H. Makabe, I. Shimoyama, G. Wu, and Y. Zhang Tetrahedron 54 1998 1095
18. T. Suzuki, K. Morita, M. Tsuchida, and K. Hiroi Org. Lett. 4 2002 2361
19. T. Suzuki, K. Morita, Y. Matsuo, and K. Hiroi Tetrahedron Lett. 44 2003 2003
20. T. Suzuki, K. Morita, M. Tsuchida, and K. Hiroi J. Org. Chem. 68 2003 1601
21. Recent examples of transfer hydrogenation using Cp*Ir complexes, see; K. Mashima, T. Abe, and K. Tani Chem. Lett. 1998 1199
22. K. Murata, T. Ikariya, and R. Noyori J. Org. Chem. 64 1999 2186
23. S. Ogo, N. Makihara, and Y. Watanabe Organometallics 18 1999 5470
24. S. Ogo, N. Makihara, Y. Kaneko, and Y. Watanabe Organometallics 20 2001 4903
25. K. Fujita, S. Furukawa, and R. Yamaguchi J. Organomet. Chem. 649 2002 289
26. K. Fujita, K. Yamamoto, and R. Yamaguchi Org. Lett. 4 2002 2691
27. T. Abura, S. Ogo, Y. Watanabe, and S. Fukuzumi J. Am. Chem. Soc. 125 2003 4149
28. K. Fujita, Z. Li, N. Ozeki, and R. Yamaguchi Tetrahedron Lett. 44 2003 2687
29. K. Fujita, C. Kitatsuji, S. Furukawa, and R. Yamaguchi Tetrahedron Lett. 45 2004 3215
30. K. Fujita, T. Fujii, and R. Yamaguchi Org. Lett. 6 2004 3525
31. F. Hanasaka, K. Fujita, and R. Yamaguchi Organometallics 23 2004 1490
32. G. Cami-Kobeci, P.A. Slatford, M.K. Whittlesey, and J.M.J. Williams Bioorg. Med. Chem. Lett. 15 2005 535
33. J.P. Richard, and R.W. Nagorsi J. Am. Chem. Soc. 121 1999 4763
34. 2: 164.0837. Found: 164.0862
35. For recent examples of Tishchenko and related reactions, see: T. Ooi, K. Ohmatsu, K. Sasaki, T. Miura, and K. Maruoka Tetrahedron Lett. 44 2003 3191
36. V. Gnanadesikan, Y. Horiuchi, T. Ohshima, and M. Shibasaki J. Am. Chem. Soc. 126 2004 7782
37. for a recent review: O.P. Törmäkangas, and A.M.P. Koskinen Recent Res. Devel. Org. Chem. 5 2001 225
38. J. Uenishi, S. Masuda, and S. Wakabayashi Tetrahedron Lett. 32 1991 5097
39. J.-L. Hsu, C.-T. Chen, and J.-M. Fang Org. Lett. 1 1999 1989
40. M. Adinolfi, G. Barone, F. De Lorenzo, and A. Iadonisi Synlett 1999 336
41. G.L. Lange, and M.G. Organ Synlett 1991 665
42. For the intramolecular Tishchenko reaction of dialdehyde, see: S.H. Bergens, D.P. Fairlie, and B. Bosnich Organometallics 9 1990 566
43. S.-y. Onozawa, T. Sakakura, M. Tanaka, and M. Shiro Tetrahedron 52 1996 4291
44. 3CN, toluene, and 2-butanone gave unsatisfactory results
45. 3): δ = 3.14 (dd, J = 16.4, 3.2 Hz, 1H), 3.36 (dd, J = 16.4, 11.9 Hz, 1H), 5.57 (dd, J = 11.9, 3.2 Hz, 1H), 7.2-7.9 (m, 8H), 8.16 (d, J = 7.6 Hz, 1H)
46. M.S. Newman, and W.M. Edwards J. Am. Chem. Soc. 76 1954 1840
47. S. Anttus, G. Snatzke, and I. Steinke Liebigs Ann. Chem. 1983 2247
48. P. Bobicelli, P. Lupattelli, B. Crescenzi, A. Sanetti, and R. Bernini Tetrahedron 55 1999 14719
49. 8f