From p-benzoquinone to cyclohexane chirons: First asymmetric synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide

Tetrahedron Asymmetry

Volumn 14, Issue 14, 2003, Pages 2021-2032

  Busqué, Felix ^a   Cantó, Mariona ^a   De March, Pedro ^a   Figueredo, Marta ^a   Font, Josep ^a   Rodríguez, Sonia ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; 1,4 BENZOQUINONE; 2 (8 HYDROXY 2,3 DIPHENYL 1,4 DIOXASPIRO[4.5]DECA 6,9 DIEN 8 YL)ACETIC ACID; 2,3 DIPHENYL 1,4 DIOXASPIRO[4.5]DECA 6,9 DIEN 8 OL; 2,3 DIPHENYL 1,4 DIOXASPIRO[4.5]DECAN 8 ONE; 3A HYDROXY 3,3A,7,7A TETRAHYDROBENZOFURAN 6(2H) ONE; 3A HYDROXY 4',5' DIPHENYL 3,3A,7,7A TETRAHYDROSPIRO[BENZOFURO 6(2H),2' [1.3]DIOXOLAN] 2 ONE; 4',5' DIPHENYL 3,3A,7,7A TETRAHYDROSPIRO[BENZOFURO 6(2H),2' [1.3]DIOXOLAN] 3A OL; 4',5' DIPHENYL 7,7A DIHYDROSPIRO[BENZOFURO 6(2H),2' [1.3]DIOXOLAN] 2 ONE; 6 HYDROXY 7,7A DIHYDROBENZOFURAN 2(6H) ONE MENISDAURILIDE; 6 OXO 7,7A DIHYDROBENZOFURAN 2(6H) ONE; 6,7:9,10 DIEPOXY 2,3 DIPHENYL 1,4 DIOXASPIRO[4.5]DECAN 8 OL; 6,7:9,10 DIEPOXY 2,3 DIPHENYL 1,4 DIOXASPIRO[4.5]DECAN 8 ONE; 8 (2 HYDROXY)ETHYL 2,3 DIPHENYL 1,4 DIOXASPIRO[4.5]DECA 6,9 DIEN 8 OL; ACETIC ACID DERIVATIVE; BENZENE DERIVATIVE; BENZOFURAN DERIVATIVE; CYCLOHEXANE DERIVATIVE; ETHYL 2 (8 HYDROXY 2,3 DIPHENYL 1,4 DIOXASPIRO[4.5]DECA 6,9 DIEN 8 YL)ACETATE; FUNCTIONAL GROUP; FURAN DERIVATIVE; MENISDAURILIDE; NATURAL PRODUCT; RENGYOLONE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; DRUG SYNTHESIS; ENANTIOMER; IODINATION; PRIORITY JOURNAL;

EID: 0037484718     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00357-4     Document Type: Article

References (81)

1. Endo K., Hikino H. Can. J. Chem. 62:1984;2011-2014.
2. Messana I., Sperandei M., Multari G., Galeffi C., Marini Bettolo G.B. Phytochemistry. 23:1984;2617-2619.
3. Llera L.D., Trujillo J.M., Breton J.L., Navarro E. J. Nat. Prod. 50:1987;251-252.
4. Kuwajima H., Takahashi M., Ito M., Wu H.-X., Takaishi K., Inoue K. Phytochemistry. 33:1993;137-139.
5. Hase T., Kawamoto Y., Ohtani K., Kasai R., Yamasaki K., Picheansoonthon C. Phytochemistry. 39:1995;235-241.
6. Limiroli R., Consonni R., Ranalli A., Bianchi G., Zetta L. J. Agric. Food Chem. 44:1996;2040-2048.
7. Jensen S.R. Biochem. Syst. Ecol. 28:2000;45-51.
8. Nishino, C.; Kobayashi, K. (Mitsubishi Kasei Corp.) JP 01,290,627, 1989 [Chem. Abstr. 1990, 112, 191943y] Nishino, C.; Kobayashi, K. (Mitsubishi Kasei Corp.) JP 01,290,666, 1989 [Chem. Abstr. 1990, 112, 235165c] Nagakura, A.; Sato, M.; Kikuchi, M.; Nakatsu, T. (Takasago Perfumery Co.) JP 02,200,631, 1990 [Chem. Abstr. 1991, 114, 30162u].
9. Takahashi K., Matsuzawa S., Takani M. Chem. Pharm. Bull. 26:1978;1677-1681.
10. Guerriero A., Pietra F. Phytochemistry. 23:1984;2394-2396.
11. Yogo M., Ishiguro S., Murata H., Furukawa H. Chem. Pharm. Bull. 38:1990;225-226.
12. Bachmann T.L., Ghia F., Torssell K.B.G. Phytochemistry. 33:1993;189-191.
13. Otsuka H., Ito A., Fujioka N., Kawamata K.I., Kasai R., Yamasaki K., Satoh T. Phytochemistry. 33:1993;389-392.
14. Ueda M., Shigemori-Suzuki T., Yamamura S. Tetrahedron Lett. 36:1995;6267-6270.
15. Sakamura S., Ito J., Sakai R. Agr. Biol. Chem. 34:1970;153-155.
16. Sakamura S., Ito J., Sakai R. Agr. Biol. Chem. 35:1971;105-110.
17. Ichihara A., Oda K., Sakamura S. Agr. Biol. Chem. 35:1971;445-446.
18. Ichihara A., Kimura R., Oda K., Moriyasu K., Sakamura S. Agr. Biol. Chem. 46:1982;1879-1883.
19. Yoshida N., Konno H., Kamikubo T., Takahashi M., Odasawara K. Tetrahedron: Asymmetry. 10:1999;3849-3857.
20. Higa T., Okuda R.K., Severns R.M., Scheuer P.J., He C.-H., Changfu X., Clardy J. Tetrahedron. 43:1987;1063-1070.
21. Gautier E.C.L., Lewis N.J., McKillop A., Taylor R.J.K. Tetrahedron Lett. 35:1994;8759-8760.
22. Johnson C.R., Miller M.W. J. Org. Chem. 60:1995;6674-6675.
23. Block O., Klein G., Altenbach H.-J., Brauer D.J. J. Org. Chem. 65:2000;716-721.
24. Roy K., Mukhopadhyay T., Reddy G.C.S., Desikan K.R., Rupp R.H., Ganguli B.N. J. Antibiot. 41:1988;1780-1784.
25. Fehlhaber H.W., Kogler H., Mukhopadhyay T., Vijayakumar E.K.S., Ganguli B.N. J. Am. Chem. Soc. 110:1988;8242-8244.
26. McKillop A., McLaren L., Taylor R.J.K., Watson R.J., Lewis N. Synlett. 1992;201-203.
27. McKillop A., McLaren L., Taylor R.J.K., Watson R.J., Lewis N.J. J. Chem. Soc., Perkin Trans. 1. 1996;1385-1393.
28. Buzzetti F., Gäumann E., Hütter R., Keller-Schierlein W., Neipp L., Prelog V., Zähner H. Pharm. Acta Helv. 38:1963;871-874.
29. Alcaraz L., Macdonald G., Ragot J.P., Lewis N., Taylor R.J.K. J. Org. Chem. 63:1998;3526-3527.
30. Taylor R.J.K., Alcaraz L., Kapfer-Eyer I., Macdonald G., Wei X., Lewis N. Synthesis. 1998;775-790.
31. Alcaraz L., Macdonald G., Ragot J.P., Lewis N.J., Taylor R.J.K. Tetrahedron. 55:1999;3707-3716.
32. Vosburg D.A., Weiler S., Sorensen E.J. Angew. Chem., Int. Ed. 38:1999;971-974.
33. Wernert N., Stanjek A., Kiriakidis S., Hugel A., Jha H.C., Mazitschek R., Giannis A. Angew. Chem., Int. Ed. 38:1999;3228-3231.
34. Taber D.F., Christos T.E., Rheingold A.L., Guzei I.A. J. Am. Chem. Soc. 121:1999;5589-5590.
35. Hutchings M., Moffat D., Simpkins N.S. Synlett. 2001;661-663.
36. Boiteau J.-G., Van de Weghe P., Eustache J. Org. Lett. 3:2001;2737-2740.
37. Baldwin J.E., Bulger P.G., Marquez R. Tetrahedron. 58:2002;5441-5452.
38. Hudlicky T., Gonzalez D., Gibson D.T. Aldrichim. Acta. 32:1999;35-62. and references cited therein.
39. Konno H., Ogasawara K. Synthesis. 1999;1135-1140.
40. Hiroya K., Zhang H., Ogasawara K. Synlett. 1999;529-532. and references cited therein.
41. Hareau G.P.-J., Koiwa M., Hikichi S., Sato F. J. Am. Chem. Soc. 121:1999;3640-3650.
42. Enders D., Nühring A., Runsink J. Chirality. 12:2000;374-377.
43. Taber D.F., Christos T.E., Rahimizadeh M., Chen B. J. Org. Chem. 66:2001;5911-5914.
44. de March P., Escoda M., Figueredo M., Font J., Alvarez-Larena A., Piniella J.F. J. Org. Chem. 60:1995;3895-3897.
45. de March P., Figueredo M., Font J., Medrano J. Tetrahedron. 55:1999;7907-7914.
46. Whitesell J.K. Chem. Rev. 89:1989;1581-1590.
47. Alexakis A., Mangeney P. Tetrahedron: Asymmetry. 1:1990;477-511.
48. Mash E.A., Hemperly S.B., Nelson K.A., Heidt P.C., Van Deusen S. J. Org. Chem. 55:1990;2045-2055.
49. Kato K., Suemune H., Sakai K. Tetrahedron Lett. 34:1993;4979-4980.
50. Ramachandran P.V., Chen G.-M., Lu Z.-H., Brown H.C. Tetrahedron Lett. 37:1996;3795-3798.
51. Takeda T., Imamoto T. Tetrahedron: Asymmetry. 10:1999;3209-3218.
52. Barrett A.G.M., Braddock D.C., de Koning P.D., White A.J.P., Williams D.J. J. Org. Chem. 65:2000;375-380.
53. Matsumoto K., Sato Y., Shimojo M., Hatanaka M. Tetrahedron: Asymmetry. 11:2000;1965-1973.
54. de March P., Escoda M., Figueredo M., Font J. Tetrahedron Lett. 36:1995;8665-8688.
55. de March P., Escoda M., Figueredo M., Font J., Alvarez-Larena A., Piniella J.F. J. Org. Chem. 62:1997;7781-7787.
56. de March P., Figueredo M., Font J., Rodríguez S. Tetrahedron. 56:2000;3603-3609.
57. de March P., Escoda M., Figueredo M., Font J., García-García E., Rodríguez S. Tetrahedron: Asymmetry. 11:2000;4473-4483.
58. Preliminary results of this work have been published: (a) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; Rodríguez, S. Tetrahedron: Asymmetry 2001, 12, 3077-3080; (b) Cantó, M.; de March, P.; Figueredo, M.; Font, J.; Rodríguez, S.; Álvarez-Larena, A.; Piniella, J. F. Tetrahedron: Asymmetry 2002, 13, 455-459.
59. Keller, R. (Hoechst AG) DE 3045680, 1982 [Chem. Abstr. 1983, 98, 34904m].
60. Gautier E.C.L., Graham A.E., McKillop A., Standen S.P., Taylor R.J.K. Tetrahedron Lett. 38:1997;1881-1884.
61. Konopelski J.P., Deng H., Schiemann K., Keane J.M., Olmstead M.M. Synlett. 1998;1105-1107.
62. Corey E.J., Wu L.I. J. Am. Chem. Soc. 115:1993;9327-9328.
63. Kamikubo T., Ogasawara K. Chem. Commun. 1996;1679-1680.
64. Graham A.E., Taylor R.J.K. J. Chem. Soc., Perkin Trans. 1. 1997;1087-1089.
65. Sirisoma N.S., Johnson C.R. Tetrahedron Lett. 39:1998;2059-2062.
66. Rezgui F., El Gaied M.M. Tetrahedron Lett. 39:1998;5965-5966.
67. Araki S., Katsumura N., Kawasaki K., Butsugan Y. J. Chem. Soc., Perkin Trans. 1. 1991;499-500.
68. Endo K., Seya K., Hikino H. Tetrahedron. 45:1989;3673-3682.
69. Bianco A., Lo Scalzo R., Scarpati M.L. Phytochemistry. 32:1993;455-457.
70. Tian J., Zhao Q.-S., Zhang H.-J., Lin Z.-W., Sun H.-D. J. Nat. Prod. 60:1997;766-769.
71. Saito I., Chujo Y., Shimazu H., Yamane M., Matsuura T., Cahnmann H.J. J. Am. Chem. Soc. 97:1975;5272-5277.
72. Schweizer J., Lattrell R., Hecker E. Experientia. 31:1975;1267-1268.
73. Breton J.L., Llera L.D., Navarro E., Trujillo J. Tetrahedron. 43:1987;4447-4451.
74. Navarro E., Alonso S.J., Boada J., Trujillo J., Ayuso M.J., Gutierrez Navarro A. Fitoterapia. 63:1992;251-254.
75. Kocovský P., Pour M. J. Org. Chem. 55:1990;5580-5589.
76. Gil J., Virgili A. J. Org. Chem. 64:1999;7274-7276.
77. Mori K., Audran G., Nakahara Y., Bando M., Kido M. Tetrahedron Lett. 38:1997;575-578.
78. Audran G., Mori K. Eur. J. Org. Chem. 1998;57-62.
79. Amos R.A., Katzenellenbogen J.A. J. Org. Chem. 43:1978;560-564.
80. Rubottom G.M., Juve H.D. Jr. J. Org. Chem. 48:1983;422-425.
81. Wang Z.-M., Sharpless K.B. J. Org. Chem. 59:1994;8302-8303.