Total synthesis of the novel, biologically active epoxyquinone dimer (±)-torreyanic acid: A biomimetic approach

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3985-3988

  Mehta, Goverdhan ^a   Pan, Subhas Chandra ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

QUINONE DERIVATIVE; TORREYANIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIELS ALDER REACTION; DIMERIZATION; DRUG SYNTHESIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 8744262720     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0483551     Document Type: Article

References (28)

1. For a recent comprehensive review, see: Marco-Contelles, J.; Molina, M. T.; Anjum, S. Chem. Rev. 2004, 104, 28572.
2. Selected examples of epoxyquinone natural products: (a) Oloigosporons: Anderson, M. G.; Jarman, T. B.; Rickards, R. W. J. Antibiot. 1995, 48, 391. (b) Panepoxydon: Erkel, G.; Anke, T.; Sterner, O. Biochem. Biophys. Res. Commun. 1996, 226, 214. (c) Cycloepoxydon: (i) Gehrt, A.; Erkel, G.; Anke, H. Anke, T.; Sterner, O. Nat. Prod. Lett. 1997, 9, 259. (ii) Gehrt, A.; Erkel, G.; Anke, T.; Sterner, O. J. Antibiot. 1998, 57, 455. (d) Yanuthones: Bugni, T. S.; Abbanat, D.; Bernan, V. S.; Maiese, W. M.; Greenstein, M.; Van Wagoner, R. M.; Ireland, C. M. J. Org. Chem. 2000, 65, 7195. (e) Ambuic acid: Li, J. Y.; Harper, J. K.; Grant, D. M.; Tombe, B. O.; Bashyal, B.; Hess, W. M.; Strobel, G. A. Phytochemistry 2001, 56, 463. (f) Jesterone: Li, J. Y.; Strobel, G. A. Phytochemistry 2001, 57, 261.
3. Selected examples of epoxyquinone natural products: (a) Oloigosporons: Anderson, M. G.; Jarman, T. B.; Rickards, R. W. J. Antibiot. 1995, 48, 391. (b) Panepoxydon: Erkel, G.; Anke, T.; Sterner, O. Biochem. Biophys. Res. Commun. 1996, 226, 214. (c) Cycloepoxydon: (i) Gehrt, A.; Erkel, G.; Anke, H. Anke, T.; Sterner, O. Nat. Prod. Lett. 1997, 9, 259. (ii) Gehrt, A.; Erkel, G.; Anke, T.; Sterner, O. J. Antibiot. 1998, 57, 455. (d) Yanuthones: Bugni, T. S.; Abbanat, D.; Bernan, V. S.; Maiese, W. M.; Greenstein, M.; Van Wagoner, R. M.; Ireland, C. M. J. Org. Chem. 2000, 65, 7195. (e) Ambuic acid: Li, J. Y.; Harper, J. K.; Grant, D. M.; Tombe, B. O.; Bashyal, B.; Hess, W. M.; Strobel, G. A. Phytochemistry 2001, 56, 463. (f) Jesterone: Li, J. Y.; Strobel, G. A. Phytochemistry 2001, 57, 261.
4. Selected examples of epoxyquinone natural products: (a) Oloigosporons: Anderson, M. G.; Jarman, T. B.; Rickards, R. W. J. Antibiot. 1995, 48, 391. (b) Panepoxydon: Erkel, G.; Anke, T.; Sterner, O. Biochem. Biophys. Res. Commun. 1996, 226, 214. (c) Cycloepoxydon: (i) Gehrt, A.; Erkel, G.; Anke, H. Anke, T.; Sterner, O. Nat. Prod. Lett. 1997, 9, 259. (ii) Gehrt, A.; Erkel, G.; Anke, T.; Sterner, O. J. Antibiot. 1998, 57, 455. (d) Yanuthones: Bugni, T. S.; Abbanat, D.; Bernan, V. S.; Maiese, W. M.; Greenstein, M.; Van Wagoner, R. M.; Ireland, C. M. J. Org. Chem. 2000, 65, 7195. (e) Ambuic acid: Li, J. Y.; Harper, J. K.; Grant, D. M.; Tombe, B. O.; Bashyal, B.; Hess, W. M.; Strobel, G. A. Phytochemistry 2001, 56, 463. (f) Jesterone: Li, J. Y.; Strobel, G. A. Phytochemistry 2001, 57, 261.
5. Selected examples of epoxyquinone natural products: (a) Oloigosporons: Anderson, M. G.; Jarman, T. B.; Rickards, R. W. J. Antibiot. 1995, 48, 391. (b) Panepoxydon: Erkel, G.; Anke, T.; Sterner, O. Biochem. Biophys. Res. Commun. 1996, 226, 214. (c) Cycloepoxydon: (i) Gehrt, A.; Erkel, G.; Anke, H. Anke, T.; Sterner, O. Nat. Prod. Lett. 1997, 9, 259. (ii) Gehrt, A.; Erkel, G.; Anke, T.; Sterner, O. J. Antibiot. 1998, 57, 455. (d) Yanuthones: Bugni, T. S.; Abbanat, D.; Bernan, V. S.; Maiese, W. M.; Greenstein, M.; Van Wagoner, R. M.; Ireland, C. M. J. Org. Chem. 2000, 65, 7195. (e) Ambuic acid: Li, J. Y.; Harper, J. K.; Grant, D. M.; Tombe, B. O.; Bashyal, B.; Hess, W. M.; Strobel, G. A. Phytochemistry 2001, 56, 463. (f) Jesterone: Li, J. Y.; Strobel, G. A. Phytochemistry 2001, 57, 261.
6. Selected examples of epoxyquinone natural products: (a) Oloigosporons: Anderson, M. G.; Jarman, T. B.; Rickards, R. W. J. Antibiot. 1995, 48, 391. (b) Panepoxydon: Erkel, G.; Anke, T.; Sterner, O. Biochem. Biophys. Res. Commun. 1996, 226, 214. (c) Cycloepoxydon: (i) Gehrt, A.; Erkel, G.; Anke, H. Anke, T.; Sterner, O. Nat. Prod. Lett. 1997, 9, 259. (ii) Gehrt, A.; Erkel, G.; Anke, T.; Sterner, O. J. Antibiot. 1998, 57, 455. (d) Yanuthones: Bugni, T. S.; Abbanat, D.; Bernan, V. S.; Maiese, W. M.; Greenstein, M.; Van Wagoner, R. M.; Ireland, C. M. J. Org. Chem. 2000, 65, 7195. (e) Ambuic acid: Li, J. Y.; Harper, J. K.; Grant, D. M.; Tombe, B. O.; Bashyal, B.; Hess, W. M.; Strobel, G. A. Phytochemistry 2001, 56, 463. (f) Jesterone: Li, J. Y.; Strobel, G. A. Phytochemistry 2001, 57, 261.
7. Selected examples of epoxyquinone natural products: (a) Oloigosporons: Anderson, M. G.; Jarman, T. B.; Rickards, R. W. J. Antibiot. 1995, 48, 391. (b) Panepoxydon: Erkel, G.; Anke, T.; Sterner, O. Biochem. Biophys. Res. Commun. 1996, 226, 214. (c) Cycloepoxydon: (i) Gehrt, A.; Erkel, G.; Anke, H. Anke, T.; Sterner, O. Nat. Prod. Lett. 1997, 9, 259. (ii) Gehrt, A.; Erkel, G.; Anke, T.; Sterner, O. J. Antibiot. 1998, 57, 455. (d) Yanuthones: Bugni, T. S.; Abbanat, D.; Bernan, V. S.; Maiese, W. M.; Greenstein, M.; Van Wagoner, R. M.; Ireland, C. M. J. Org. Chem. 2000, 65, 7195. (e) Ambuic acid: Li, J. Y.; Harper, J. K.; Grant, D. M.; Tombe, B. O.; Bashyal, B.; Hess, W. M.; Strobel, G. A. Phytochemistry 2001, 56, 463. (f) Jesterone: Li, J. Y.; Strobel, G. A. Phytochemistry 2001, 57, 261.
8. Selected examples of epoxyquinone natural products: (a) Oloigosporons: Anderson, M. G.; Jarman, T. B.; Rickards, R. W. J. Antibiot. 1995, 48, 391. (b) Panepoxydon: Erkel, G.; Anke, T.; Sterner, O. Biochem. Biophys. Res. Commun. 1996, 226, 214. (c) Cycloepoxydon: (i) Gehrt, A.; Erkel, G.; Anke, H. Anke, T.; Sterner, O. Nat. Prod. Lett. 1997, 9, 259. (ii) Gehrt, A.; Erkel, G.; Anke, T.; Sterner, O. J. Antibiot. 1998, 57, 455. (d) Yanuthones: Bugni, T. S.; Abbanat, D.; Bernan, V. S.; Maiese, W. M.; Greenstein, M.; Van Wagoner, R. M.; Ireland, C. M. J. Org. Chem. 2000, 65, 7195. (e) Ambuic acid: Li, J. Y.; Harper, J. K.; Grant, D. M.; Tombe, B. O.; Bashyal, B.; Hess, W. M.; Strobel, G. A. Phytochemistry 2001, 56, 463. (f) Jesterone: Li, J. Y.; Strobel, G. A. Phytochemistry 2001, 57, 261.
9. (a) Lee, J. C.; Yang, X.; Schwartz, M.; Strobel. G. A.; Clardy, J. J. Chem. Biol. 1995, 2, 721.
10. (b) Lee, J. C.; Strobel, G. A.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1996, 61, 3232.
11. (a) Li, C.; Lobkovsky, E.; Porco, J. A., Jr. J. Am. Chem. Soc. 2000, 122, 10484.
12. (b) Li, C.; Johnson, R. P.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 5095.
13. (a) Mehta, G.; Islam, K. Tetrahedron Lett. 2003, 44, 3569.
14. (b) Mehta, G.: Ramesh, S. S. Tetrahedron Lett. 2004, 45, 1985.
15. (c) Mehta, G.; Islam, K. Org. Lett. 2004, 6, 807.
16. (c) Mehta, G.; Pan, S. C. Org. Lett. 2004, 6, 811.
17. (d) Mehta, G.; Islam, K. Tetrahedron Lett. 2004, 45, 3611.
18. (e) Mehta, G.; Roy, S. Org. Lett. 2004, 6, 2389.
19. For recent reviews on biomimetic Diels-Alder reactions, see: (a) Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078. (b) de la Torre, M. C.; Sierra, M. A. Angew. Chem., Int. Ed. 2004, 43, 160.
20. For recent reviews on biomimetic Diels-Alder reactions, see: (a) Stocking, E. M.; Williams, R. M. Angew. Chem., Int. Ed. 2003, 42, 3078. (b) de la Torre, M. C.; Sierra, M. A. Angew. Chem., Int. Ed. 2004, 43, 160.
21. Allylated benzoquinone 8 was prepared from p-methoxyphenol according to a new route devised by us involving Claisen rearrangement and CAN oxidation. For earlier preparation, see: (a) Shuki, A.; Nobuhito, K.; Yasuo, B. J. Organomet. Chem. 1991, 415, 7. (b) Fausta, C.; Francesca, F.; Edoardo, L.; Francesco, M. Chem. Lett. 1992, 7, 1299 and references therein.
22. Allylated benzoquinone 8 was prepared from p-methoxyphenol according to a new route devised by us involving Claisen rearrangement and CAN oxidation. For earlier preparation, see: (a) Shuki, A.; Nobuhito, K.; Yasuo, B. J. Organomet. Chem. 1991, 415, 7. (b) Fausta, C.; Francesca, F.; Edoardo, L.; Francesco, M. Chem. Lett. 1992, 7, 1299 and references therein.
23. 13C NMR, and HRMS). See Supporting Information for experimental details and spectral data.
24. Semmelhack, M. F.; Schmid, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374.
25. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
26. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
27. While torreyanic acid ester 25 originates from the endo-selective heterodimerization of racemic 23 and 24 with the two n-pentyl chains positioned on opposite faces to minimize the steric interaction, the "iso" torreyanic acid framework is derived through heterochiral dimerization of either 23 or 24, and here again the two alkyl chains are located far apart.
28. 4b