Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antiinflammatory agent mangicol A

Tetrahedron

Volumn 62, Issue 22, 2006, Pages 5178-5194

  Pichlmair, Stefan ^a   de Lera Ruiz, Manuel ^a   Basu, Kallol ^a   Paquette, Leo A ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Chiral nonracemic substituted cyclopentadienones; Enantioselective diene synthesis; Intramolecular aldol cyclizations; Mangicols; Pd catalyzed enyne cyclization

Indexed keywords

ANTIINFLAMMATORY AGENT; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTENE DERIVATIVE; LEWIS ACID; MANGICOL A; PALLADIUM; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CROSS LINKING; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; THERMAL STIMULATION;

BETULACEAE;

EID: 33646136252     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.096     Document Type: Article

References (94)

1. Renner M.K., Jensen P.R., and Fenical W. J. Org. Chem. 63 (1998) 8346
2. Renner M.K., Jensen P.R., and Fenical W. J. Org. Chem. 65 (2000) 4843
3. At 81% in edema levels, 1 compares well with the existing widely distributed antiinflammatory agent indomethacin (71% reduction).
4. Araki K., Saito K., Arimoto H., and Uemura D. Angew. Chem., Int. Ed. 43 (2004) 81
5. Reviews:
6. Oikawa O. Yuki Gosei Kagaku Kyokaishi 62 (2004) 778
7. Oikawa O., and Tokiwano T. Nat. Prod. Rep. 3 (2004) 321
8. Pohnert G. ChemBioChem 4 (2003) 713
9. Stocking E.M., and Williams R.M. Angew. Chem., Int. Ed. 42 (2003) 3078
10. Pohnert G. ChemBioChem 2 (2001) 873
11. For examples, see:
12. Tarasow T.M., Kellogg E., Holley B.L., Nieuwlandt D., Tarasow S.L., and Eaton B.E. J. Am. Chem. Soc. 126 (2004) 11843
13. Huang X.-H., van Soest R., Roberge M., and Andersen R. Org. Lett. 6 (2004) 75
14. Stuhlmann F., and Jaeschke A. J. Am. Chem. Soc. 124 (2002) 3238
15. Seelig B., Keiper S., Stuhlmann F., and Jäschke A. Angew. Chem., Int. Ed. 39 (2000) 4576
16. Bailey W.F., and Punzalan E.R. J. Org. Chem. 55 (1990) 5404
17. Comins D.L., Zhang Y.-M., and Zheng X. Chem. Commun. (1998) 2509
18. Maradyn D.J., and Weedon A.C. J. Am. Chem. Soc. 117 (1995) 5359
19. Shapiro R.H. Org. React. 23 (1976) 1976
20. Chamberlin A.R., and Bloom S.H. Org. React. 39 (1990) 1
21. Review:. Crimmins M.T., and Reinhold T.L. Org. React. 44 (1993) 297
22. Bach T., Kemmler M., and Herdtweck E.J. J. Org. Chem. 68 (2003) 1994
23. Mattay J., Banning A., Bischof E.W., Heidbreder A., and Runsink J. Chem. Ber. 125 (1992) 2119
24. Westermann B., Scharmann H.G., and Kortmann I. Tetrahedron: Asymmetry 4 (1993) 2119
25. Torii S., Inokuchi T., Mizuguchi K., and Yamazaki M. J. Org. Chem. 44 (1979) 2303
26. Birman V.B., and Danishefsky S.J. J. Am. Chem. Soc. 124 (2002) 2080
27. Paquette L.A., Duan M., Konetzki I., and Kempmann C. J. Am. Chem. Soc. 124 (2002) 4257
28. Basu K., Richards J., and Paquette L.A. Synthesis (2004) 2841
29. Wang Z. Tetrahedron Lett. 30 (1989) 6611
30. Evans D.A. Aldrichimica Acta 15 (1982) 23
31. Evans D.A., Morrissey M.M., and Dorow R.L. J. Am. Chem. Soc. 107 (1985) 4346
32. Wang Z. Tetrahedron Lett. 30 (1989) 6611
33. Wang Z. Tetrahedron Lett. 32 (1991) 4631
34. Arvanitis E., Motevalli M., and Wyatt P.B. Tetrahedron Lett. 37 (1996) 4277
35. Winkler J.D., Holland J.M., Kasparek J., and Axelsen P.H. Tetrahedron 55 (1999) 8199
36. Harmat N.J.S., Mangani S., Perrotta E., Giannotti D., Nannicini R., and Altamura M. Tetrahedron Lett. 41 (2000) 1261
37. Wee A.G.H., and Yu Q. J. Org. Chem. 66 (2001) 8935
38. Luche J.-L. J. Am. Chem. Soc. 100 (1978) 2226
39. Gemal A.L., and Luche J.-L. J. Am. Chem. Soc. 103 (1981) 5454
40. Srikrishna A., and Hememalini P. J. Org. Chem. 55 (1990) 4883
41. Nakajima N., Horita K., Abe R., and Yonemitsu O. Tetrahedron Lett. 29 (1988) 4139
42. Hanessian S., Ugolini A., Dube D., Hodges P.J., and Andre C. J. Am. Chem. Soc. 108 (1986) 2776
43. White J.D., and Amedio J.C. J. Org. Chem. 54 (1989) 736
44. Paterson I., and Tudge M. Angew. Chem., Int. Ed. 42 (2003) 343
45. 3, HMPA, 100 °C. In all cases, a reduction in temperature returned unchanged 37.
46. Reich H.J., and Wollowitz S.J. J. Am. Chem. Soc. 104 (1982) 7051
47. Wang T.-Z., and Paquette L.A. J. Org. Chem. 51 (1986) 5232
48. Paquette L.A., Wang T.-Z., Luo J., Cottrell C.E., Clough A.E., and Anderson L.B. J. Am. Chem. Soc. 112 (1990) 239
49. Basu, K. unpublished observations.
50. Katsuki T., and Sharpless K.B. J. Am. Chem. Soc. 102 (1980) 5974
51. Rossiter B.E., Katsuki T., and Sharpless K.B. J. Am. Chem. Soc. 103 (1981) 464
52. Martin V.S., Woodard S.S., Katsuki T., Yamada Y., Ikeda M., and Sharpless K.B. J. Am. Chem. Soc. 103 (1981) 6237
53. Liu Z., Lan J., and Li Y. Tetrahedron: Asymmetry 9 (1998) 3755
54. For R3=Bn, see:
55. Doubsky S., Streinz L., Saman D., Zednik J., and Koutek B. Org. Lett. 6 (2004) 4909
56. Sato A., Kinosita H., Shinokubo H., and Oshima K. Org. Lett. 6 (2004) 2217
57. Takami K., Mikami S., Yorimitsu H., Shinokubo H., and Oshima K. J. Org. Chem. 68 (2003) 6627
58. Krafft M.E., Hirosawa C., Dalal N., Ramsey C., and Stiegman A. Tetrahedron Lett. 42 (2001) 7733
59. Andrews J.C., Crawford T.C., and Bacon B.E. J. Org. Chem. 46 (1981) 2976
60. Hubschwerlein C. Synthesis (1986) 962
61. Brückner R. Tetrahedron Lett. 29 (1988) 5747
62. At higher temperatures, a significant amount of diprotected product was isolated.
63. Review:. Chai Y., Hong S., Lindsay H.A., McFarland C., and McIntosh M.C. Tetrahedron 58 (2002) 2905
64. For procedural details, consult. Ariza X., Garcia J., Lopez M., and Montserrat L. Synlett (2001) 120
65. Carreira E.M., Frantz D.E., and Fassler R. J. Am. Chem. Soc. 122 (2000) 1806
66. Anand N.K., and Carreira E.M. J. Am. Chem. Soc. 123 (2001) 9687
67. Parker K.A., and Ledeboer M.W. J. Org. Chem. 61 (1996) 3214 and references therein
68. Trost B.M., and Krische M.J. Synlett (1998) 1
69. Aubert C., Buisine O., and Malacria M. Chem. Rev. 102 (2002) 813
70. Trost B.M. Acc. Chem. Res. 23 (1990) 34
71. Trost B.M., Romero D.L., and Rise F. J. Am. Chem. Soc. 116 (1994) 4268
72. Trost B.M., Tanoury G.J., Lautens M., Chan C., and MacPherson D.T. J. Am. Chem. Soc. 116 (1994) 4255
73. Trost B.M., and Chung J.T.L. J. Am. Chem. Soc. 107 (1985) 4586
74. Trost B.M., and Lee D.C. J. Org. Chem. 54 (1989) 2271
75. Holzapfel C.W., Lizel M., and Toerien F. Tetrahedron 55 (1999) 3467
76. Negishi E., Holmes S.J., Tour J.M., Miller J.A., Cederbaum F.E., Swanson D.R., and Takahashi T. J. Am. Chem. Soc. 111 (1989) 3336
77. Krafft M.E., Wilson A.M., Dasse O.A., Bonaga L.V.R., Cheung Y.Y., Fu Z., Shao B., and Scott I.L. Tetrahedron Lett. 39 (1998) 5911
78. Bear B.R., Sparks S.M., and Shea K.J. Angew. Chem., Int. Ed. 40 (2001) 820
79. 2 at 0 °C or below, and the like.
80. Ruiz, M. de L., unpublished observations.
81. Ramadrandran P.V., Chen G.-M., and Brown H.C. J. Org. Chem. 61 (1996) 88
82. Wright J., Drtina G.J., Roberts R.A., and Paquette L.A. J. Am. Chem. Soc. 110 (1988) 5806
83. Toyama K., Iguchi S., Sakazaki H., Oishi T., and Hirama M. Bull. Chem. Soc. Jpn. 74 (2001) 997
84. Grinsteiner T., and Yoshito K. Tetrahedron Lett. 35 (1994) 8337
85. Liu H.-J., Ulibarri G., and Browne E.N.C. Can. J. Chem. 70 (1992) 1545
86. Jung M.E., and Davidov P. Angew. Chem., Int. Ed. 41 (2002) 4125
87. Baker R., Selwood D.L., Swain C.J., and Webster N.M.H. J. Chem. Soc., Perkin Trans. 1 (1988) 471
88. Ireland R.E., Thompson W.J., Mandel N.S., and Mandel G.S. J. Org. Chem. 44 (1979) 3583
89. For examples:. Ichihara A., Kimura R., Moriyasu K., and Sakamura S. Tetrahedron Lett. 49 (1977) 4331
90. Danishefsky S., and Kitahara T. J. Am. Chem. Soc. 96 (1974) 7807
91. Jung M.E., McCombs C.A., and Charles A. Tetrahedron Lett. 34 (1976) 2935
92. Caine D., Harrison C.R., and VanDerveer D.J. Tetrahedron Lett. 24 (1983) 1353
93. O'Connor P.D., Mander L.N., and McLachlan M.M.W. Org. Lett. 6 (2004) 703
94. Roush W.R. In: Trost B.M., Fleming I., and Paquette L.A. (Eds). Comprehensive Organic Synthesis, Vol. 5 (1992), Pergamon, Oxford 513-550