Asymmetric synthesis of complicated bicyclic and tricyclic polypropanoates via the double Diels-Alder addition of 2,2′-ethylidenebis[3,5-dimethylfuran]

Helvetica Chimica Acta

Volumn 84, Issue 2, 2001, Pages 431-472

  Marchionni, Chiara ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

1 (ETHOXYCARBONYL) 1,3,4,7,8,9,10,11,12,12A DECAHYDRO 3,11 DIHYDROXY 2,4,5,7,9 PENTAMETHYL 12 OXO 2H,5H 2,4A:6,9:6,11 TRIEPOXYBENZOCYCLODECENE 10,8 CARBOLACTONE; 1,10 BIS(ACETOXYMETHYL)TETRADECAHYDRO 8 (METHOXYMETHOXY) 2,4,5,7,9 PENTAMETHYL 3,9 BIS[(2 (TRIMETHYLSILYL)ETHOXY)METHOXY] 6,11 EPOXYCYCLODECENE 4A,6,11,12 TETROL; 2,2' ETHYLIDENEBIS(3,5 DIMETHYLFURAN); 3,5 BIS(ACETOXYMETHYL) 4A,8A DIHYDROXY 1 (METHOXYMETHOXY) 2,6,8,9,10A PENTAMETHYL 2,7 BIS[(2 (TRIMETHYLSILYL)ETHOXY)METHOXY]DODECAHYDROPHENANTHRENE 4,10 DIONE; BICYCLO COMPOUND; DICARBOXYLIC ACID DERIVATIVE; FURAN DERIVATIVE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; REACTION ANALYSIS; SYNTHESIS;

EID: 0035090907     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20010228)84:2<431::AID-HLCA431>3.0.CO;2-W     Document Type: Article

References (109)

1. D. O' Hagan, 'The Polyketide Metabolites', Ellis Horwood, Chichester, 1991;
2. D. Schummer, B. Böhlendorf, M. Kiffe, G. Höfle, in 'Antibiotics and Antiviral Compounds', Eds. K. Kroh, H. A. Kirst, and H. Maag, VCU, Weinheim, 1993;
3. R. D. Norcross, I. Paterson, Chem. Rev. 1995, 95, 2041.
4. J. Staunton, Angew. Chem., Int. Ed. 1991, 30, 1302;
5. D. O'Hagan, Nat. Prop. Rep. 1995, 12, 1;
6. C. J. Dutton, B. J. Banks, C. B. Cooper, Nat. Prop. Rep. 1995, 12, 165;
7. L. Katz, Chem. Rev. 1997, 97, 2557;
8. J. Staunton, B. Wilkinson, Chem. Rev. 1997, 97, 2611.
9. P. F. Leadlay, Curr. Opin. Chem. Biol. 1997, 1, 162;
10. C. Khosla, Chemtracts-Org. Chem. 1998, 11, 1.
11. P. Kernen, P. Vogel, Helv. Chim. Acta 1995, 78, 301.
12. J. Ancerewicz, P. Vogel, Helv. Chim. Acta 1996, 79, 1393.
13. See, e.g., I. Paterson, J. P. Scott, J. Chem. Soc., Perkin Trans. 1 1999, 1003;
14. I. Paterson, D. Trillyer, J. Org. Chem. 1993, 58, 4182;
15. A. Abiko, J.-F. Liu, S. Masamune, J. Am. Chem. Soc. 1997, 119, 2586;
16. A. B. Smith, III, M. D. Kaufmann, T. J. Beauchamp, M. J. LaMarche, H. Arimoto, Org. Lett. 1999, 1, 1823.
17. K. C. Nicolaou, J. Xu, F. Murphy, S. Barluenga, O. Baudoin, H.-x. Wei, D. L. F. Gray, T. Ohshima, Angew. Chem., Int. Ed. 1999, 38, 2447.
18. D. A. Evans, J. S. Clark, R. Metternich, V. J. Nozack, G. S. Sheppard, J. Am. Chem. Soc. 1990, 112, 866;
19. D. A. Evans, H. P. Ng, J. S. Clark, D. L. Rieger, Tetrahedron 1992, 48, 2127;
20. D. A. Evans, A. S. Kim, R. Metternich, V. J. Novack, J. Am. Chem. Soc. 1998, 120, 5921;
21. I. Paterson, R. D. Tillyer, Tetrahedron Lett. 1992, 33, 4233.
22. R. Mahrwald, B. Ziemer, Tetrahedron 1999, 55, 14005;
23. G. A. Sulikowski, W.-M. Lee, B. Jin, B. Wu, Org. Lett. 2000, 2, 1439.
24. See, e.g. W. R. Roush, A. D. Palkowitz, K. Ando, J. Am. Chem. Soc. 1990, 112, 6348;
25. W. R. Roush, K. Koyama, M. L. Curtin, K. J. Moriarty, J. Am. Chem. Soc. 1996, 118, 7502;
26. R. W. Hoffmann, U. Rolle, R. Göttlich, Liebigs Ann. Chem. 1996, 1717;
27. G. R. Scarlato, J. A. DeMattei, L. S. Chong, A. K. Ogawa, M. R. Lin, R. W. Armstrong, J. Org. Chem. 1996, 61, 6139;
28. S. D. Rychnovsky, C. R. Thomas, Org. Lett. 2000, 2, 1217.
29. See, e.g., N. F. Jain, N. Takenaka, J. S. Panek, J. Am. Chem. Soc. 1996, 118, 12475;
30. J. S. Panek, N. F. Jain, J. Org. Chem. 1998, 63, 4572;
31. S. R. Chemler, W. R. Roush, J. Org. Chem. 1998, 63, 3800;
32. S. R. Chemler, W. R. Roush, Tetrahedron Lett. 1999, 40, 4643.
33. J. A. Marshall, M. R. Palovich, J. Org. Chem. 1998, 63, 3701;
34. J. A. Marshall, R. N. Fitzgerald, J. Org. Chem. 1999, 64, 4477.
35. J. A. Marshall, N. D. Adams, J. Org. Chem. 1999, 5201.
36. T. R. Hoye, D. R. Peck, T. A. Swanson, J. Am. Chem. Soc. 1984, 106, 2738;
37. T. Harada, Y. Kagamihara, S. Tanaka, K. Sakamoto, A. Oku, J. Org. Chem. 1992, 57, 1637;
38. C. S. Poss, S. L. Schreiber, Acc. Chem. Res. 1994, 27, 9;
39. S. D. Rychnovsky, G. Griesgraber, J. Kim, J. Am. Chem. Soc. 1994, 116, 2621;
40. R. Chênevert, G. Courchesne, Tetrahedron Lett. 1995, 6, 2093;
41. S. R. Magnusson, Tetrahedron 1995, 51, 2167;
42. W. Oppolzer, J. De Brabander, W. Walther, G. Bernardinelli, Tetrahedron Lett. 1995, 36, 4413;
43. J. N. Shepherd, J. Na, D. C. Myles, J. Org. Chem. 1997, 62, 4558;
44. M. V. Perkins, R. A. Sampson, Tetrahedron Lett. 1998, 39, 8367;
45. S. Hanessian, J. Ma, W. Wang, Tetrahedron Lett. 1999, 40, 4627;
46. D. E. Ward, C. Guo, P. K. Sasmal, C. C. Man, M. Sales, Org. Lett. 2000, 2, 1325.
47. S. Masamune, C. U. Kim, K. E. Wilson, G. O. Spessard, P. E. Georghiou, G. S. Bates, J. Am. Chem. Soc. 1975, 97, 3512;
48. J. D. White, Y. Fukuyama, J. Am. Chem. Soc. 1979, 101, 226;
49. P. A. Grieco, Y. Ohfune, Y. Yokayama, W. Owens, J. Am. Chem. Soc. 1979, 101, 4749;
50. P. A. Grieco, J. Inanaga, N.-H. Lin, T. Yanami, J. Am. Chem. Soc. 1982, 104, 5781;
51. M. G. D. Drew, J. Mann, H. J. Holland, H. J. Lewis, J. Chem. Res. (S) 1987, 3101;
52. M. Lautens, Synlett 1993, 177;
53. M. Lautens, Pure Appl. Chem. 1992, 64, 1873;
54. P. Chiu, M. Lautens, Top. Curr. Chem. 1997, 190, 1;
55. M. Lautens, S. Ma, J. Org. Chem. 1996, 61, 7246;
56. M. Lautens, S. Ma, P. Chiu, J. Am. Chem. Soc. 1997, 119, 6478;
57. M. Lautens, T. Rovis, N. D. Smith, D. Ostrovsky, Pure Appl. Chem. 1998, 70, 1059;
58. M. Lautens, J.-L. Renaud, S. Hiebert, J. Am. Chem. Soc. 2000, 122, 1804;
59. A. M. Montaña, F. Garcia, P. M. Orima, Tetrahedron 1999, 55, 5483;
60. O. Arjona, A. Martin-Domenech, J. Plumet, J. Org. Chem. 1993, 58, 7929;
61. J. L. Aceña, O. Arjona, M. León, J. Plumet, Tetrahedron Lett. 1996, 37, 8957;
62. J. S. Yadav, C. S. Rao, S. Chandrasekhar, A. V. RamaRao, Tetrahedron Lett. 1995, 36, 7712;
63. M. Lautens, P. Chiu, J. T. Colucci, Angew. Chem., Int. Ed. 1993, 32, 281;
64. J. L. Aceña, O. Arjona, M. León, J. Plumet, Tetrahedron Lett. 1996, 37, 8957;
65. O. Arjona, R. Menchaca, J. Plumet, Tetrahedron Lett. 1998, 39, 6753;
66. J. H. Rigby, K. R. Fales, Tetrahedron Lett. 1998, 39, 5717.
67. P. Kernen, P. Vogel, Tetrahedron Lett. 1993, 34, 2473.
68. A.-F. Sevin, P. Vogel, J. Org. Chem. 1994, 59, 5920;
69. P. Kernen, P. Vogel, Helv. Chim. Acta 1995, 78, 325.
70. M. Bialecki, P. Vogel, Helv. Chim. Acta 1995, 78, 325.
71. P. Vogel, A.-F. Sevin, P. Kernen, M. Bialecki, Pure Appl. Chem. 1996, 68, 719.
72. J. Ancerewicz, P. Vogel, Helv. Chim. Acta 1996, 79, 1393.
73. C. Marchionni, P. Vogel, P. Roversi, Tetrahedron Lett. 1996, 37, 4149.
74. C. Marchionni, K. Meilert, P. Vogel, K. Schenk, Synlett 2000, 8, 1111.
75. P. Vogel, J. Cossy, J. Plumet, O. Arjona, Tetrahedron 1999, 55, 13521.
76. T. Tsunoda, M. Suzuki, R. Noyori, Tetrahedron Lett. 1980, 21, 1357;
77. J. R. Hwu, L. C. Leu, J. A. Robl, D. A. Anderson, J. M. Wetzel, J. Org. Chem. 1987, 52, 188.
78. P. K. Jadhav, H. C. Brown, J. Org. Chem. 1981, 46, 2988;
79. P. Herold, P. Mohr, C. Tamm, Helv. Chim. Acta 1983, 66, 744.
80. H. C. Brown, P. K. Jadhav, A. K. Mandal, J. Org. Chem. 1982, 47, 5074;
81. H. C. Brown, B. Singaram, J. Am. Chem. Soc. 1984, 106, 1797;
82. A. Pelter, K. Smith, H. C. Brown, 'Borane Reagents', Academic Press, 1988.
83. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1968, 90, 3732;
84. J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543.
85. H. J. C. Yeh, S. K. Balani, H. Yagi, R. M. E. Greene, N. D. Sharma, D. R. Boyd, D. M. Jerina, J. Org. Chem. 1986, 51, 5439;
86. L. M. Sweeting, D. C. Crans, G. M. Whitesides, J. Org. Chem. 1987, 52, 2273.
87. H. C. Brown, M. C. Desai, P. K. Jadhav, J. Org. Chem. 1982, 47, 5065;
88. H. C. Brown, B. Singaram, J. Org. Chem. 1984, 49, 945.
89. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512;
90. D. E. Ward, C. K. Rhee, Tetrahedron Lett. 1991, 32, 7165.
91. E. J. Corey, R. K. Bakshi, S. Shibata, C.-P. Chen, V. K. Singh, J. Am. Chem. Soc. 1987, 109, 7925;
92. E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551;
93. E. J. Corey, J. O. Link, J. Am. Chem. Soc. 1992, 114, 1906;
94. E. J. Corey, J. O. Link, Tetrahedron Lett. 1992, 33, 4141;
95. E. J. Corey, C. J. Helal, Angew. Chem., Int. Ed. Engl. 1998, 37, 1986.
96. A. Alexakis, J. C. Frutos, P. Mangeney, Tetrahedron: Asymmetry 1993, 4, 2431.
97. C. R. Johnson, J. R. Zeller, J. Am. Chem. Soc. 1982, 104, 4021.
98. L. Brown, M. Koreeda, J. Org. Chem. 1984, 49, 3875.
99. N. Harada, K. Nakanishi, Acc. Chem. Res. 1972, 5, 257;
100. 'Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry', University Science Books, Oxford University Press, Oxford, UK, 1983.
101. J.-L. Luche, A. L. Gemal, J. Am. Chem. Soc. 1979, 101, 58.
102. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936.
103. J. Cossy, J. L. Ranaivosata, V. Bellosta, J. Ancerewicz, R. Ferritto, P. Vogel, J. Org. Chem. 1995, 60, 8351.
104. D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560;
105. D. A. Evans, K. T. Chapman, Tetrahedron Lett. 1986, 27, 5939.
106. K. Kraehenbuehl, S. Picasso, P. Vogel, Helv. Chim. Acta 1998, 81, 1439.
107. F. Straus, Chem. Ber. 1904, 37.
108. H. Midorikowa, Bull. Chem. Soc. Jpn. 1953, 26, 302.
109. D. G. Barrett, G. Liang, D. T. McQuade, J. M. Desper, K. D. Schladetzky, S. H. Gellmann, J. Am. Chem. Soc. 1994, 116, 10525.