Total synthesis of the epoxyquinol dimer (+)-panepophenanthrin: application of a diastereospecific biomimetic Diels-Alder dimerisation

Tetrahedron

Volumn 62, Issue 42, 2006, Pages 9892-9901

  Comméiras, Laurent ^a   Moses, John E ^a   Adlington, Robert M ^a   Baldwin, Jack E ^a   Cowley, Andrew R ^a   Baker, Christopher M ^a   Albrecht, Birgit ^a   Grant, Guy H ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Biomimetic synthesis; Dimerisation cascade; Epoxyquinol; Stille coupling; Total synthesis; Ubiquitin activating enzyme E1

Indexed keywords

NATURAL PRODUCT; PANEPOPHENANTHRIN; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; DIELS ALDER REACTION; DIMERIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOSPECIFICITY; STILLE REACTION;

BETULACEAE;

EID: 33748168241     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.08.010     Document Type: Article

References (58)

1. Sekizawa R., Ikeno S., Nakamura H., Naganawa H., Matsui S., Iinuma H., and Takeuchi T. J. Nat. Prod. 65 (2002) 1491
2. Tsukamoto S., Hirota H., Imachi M., Fujimuro M., Onuki H., Ohta T., and Yokosawa H. Bioorg. Med. Chem. Lett. 15 (2005) 191
3. For an overview of the ubiquitination pathway, see:
4. Hershko A., and Ciechanover A. Annu. Rev. Biochem. 67 (1998) 425
5. For a discussion of E1 as a potential drug target, see:
6. Swinney D.C. Drug Discov. Today 6 (2001) 244
7. Nagasawa H., Suzuki A., and Tamura S. Agric. Biol. Chem. 42 (1978) 1303
8. Higa T., Okuda R.K., Severns R.M., Scheur P.J., He C.-H., Changfu X., and Clardy J. Tetrahedron 43 (1987) 1063
9. Li J.Y., and Strobel G.A. Phytochemistry 57 (2001) 261
10. Buzzetti F., Gaumann E., Hutter R., Keller-Schierlein W., Neipp L., Prelog V., and Zahner H. Pharm. Acta Helv. 38 (1963) 871
11. Hara M., Akasaka K., Akinaga S., Okabe M., Nakano H., Gomez R., Wood D., Uh M., and Tamanoi F. Proc. Natl. Acad. Sci. U.S.A. 90 (1993) 2281
12. Hara M., and Han M. Proc. Natl. Acad. Sci. U.S.A. 92 (1995) 3333
13. Lee J.C., Yang X., Schwartz M., Strobel G.A., and Clardy J. Chem. Biol. 2 (1995) 721
14. Lee J.C., Strobel G.A., Lobkovsky E., and Clardy J. J. Org. Chem. 61 (1996) 3232
15. Kakeya H., Onose R., Koshino H., Yoshida A., Kobayashi K., Kageyama S.-I., and Osada H. J. Am. Chem. Soc. 124 (2002) 3496
16. Kakeya H., Onose R., Yoshida A., Koshino H., and Osada H. J. Antibiot. 55 (2002) 829
17. Li C., and Porco Jr. J.A. J. Org. Chem. 70 (2005) 6053
18. Liang M.-C., Bardhan S., Li C., Pace E.A., Porco Jr. J.A., and Gilmore T.D. Mol. Pharmacol. 64 (2003) 123
19. Li C., Johnson R.P., and Porco Jr. J.A. J. Am. Chem. Soc. 125 (2003) 5095
20. Li C., Bardhan S., Pace E.A., Liang M.-C., Gilmore T.D., and Porco Jr. J.A. Org. Lett. 4 (2002) 3267
21. Hu Y., Li C., Kulkarni B.A., Strobel G., Lobkovsky E., Torczynski R.M., and Porco Jr. J.A. Org. Lett. 3 (2001) 1649
22. Li C., Lobkovsky E., and Porco Jr. J.A. J. Am. Chem. Soc. 122 (2000) 10484
23. Shoji M., Kishida S., Kodera Y., Shiina I., Kakeya H., Osada H., and Hayashi Y. Tetrahedron Lett. 44 (2003) 7205
24. Shoji M., Imai H., Shiina I., Kakeya H., Osada H., and Hayashi Y. J. Org. Chem. 69 (2004) 1548
25. Nagata T., Ando Y., and Hirota H. Biosci. Biotechnol. Biochem. 56 (1992) 810
26. Kawazi, K.; Kobayashi, A.; Oe, K. JP 03 41 075.
27. Chem. Abstr. 115 (1991) 181517k
28. Kobayashi, A.; Ooe, K.; Yata, S.; Kawazu, K. Symposiumof papers, the 31st Symposium on the Chemistry of Natural Products, Nagoya, October 1989, 388.
29. Moses J.E., Commeiras L., Baldwin J.E., and Adlington R.M. Org. Lett. 5 (2003) 2987
30. Heathcock C.H. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 14323
31. Moses J.E., and Adlington R.M. Chem. Commun. (2005) 5945
32. Wipf P., Jeger P., and Kim Y. Bioorg. Med. Chem. Lett. 8 (1998) 351
33. For Diels-Alder dimerisation reactions of 2-vinylcyclohexenones and related dienes, see:
34. Spino C., Pesant M., and Dory Y. Angew. Chem., Int. Ed. 37 (1998) 3262
35. For example, see:
36. Whittle Y.G., and Gould S.J. J. Am. Chem. Soc. 109 (1987) 5043
37. Gould S.J., Shen B., and Whittle Y.G. J. Am. Chem. Soc. 111 (1989) 7932
38. Lindsey C.C., Gómez-Díaz C., Villalba J.M., and Pettus T.R.R. Tetrahedron 58 (2002) 4559
39. Shotwell J.B., Hu S., Medina E., Abe M., Cole R., Crews C.M., and Wood J.L. Tetrahedron Lett. 41 (2000) 9639
40. Kis V.Z., Closse A., Sigg H., Hruban L., and Snatzke G. Helv. Chim. Acta 53 (1970) 1577
41. Erkel G., Anke T., and Sterner O. Biochem. Biophys. Res. Commun. 226 (1996) 214
42. Graham A.E., McKerrecher D., Davies D.H., and Taylor R.J.K. Tetrahedron Lett. 37 (1996) 7445
43. Graham A.E., and Taylor R.J.K. J. Chem. Soc., Perkin Trans. 1 (1997) 1087
44. Miller M.W., and Johnson C.R. J. Org. Chem. 62 (1997) 1582
45. Kamikubo T., and Ogasawara K. Chem. Commun. (1996) 1679
46. Johnson C.R., and Miller M.W. J. Org. Chem. 60 (1995) 6674
47. Zhang H.X., Guibé F., and Balavoine G. J. Org. Chem. 55 (1990) 1857
48. Block O., Klein G., Altenbach H.-J., and Brauer D.J. J. Org. Chem. 65 (2000) 716
49. Adelt S., Plettenburg O., Stricker R., Reiser G., Altenbach H.-J., and Vogel G. J. Med. Chem. 42 (1999) 1262
50. Altenbach H.-J., Stegelmeir H., and Vogel G. Tetrahedron Lett. 31 (1978) 3333
51. Kienzle F., Stadlwieser J., Rank W., and Mergelsberg I. Tetrhedron Lett. 29 (1988) 6479
52. Lei X., Johnson R.P., and Porco Jr. J.A. Angew. Chem., Int. Ed. 42 (2003) 3913
53. Mehta G., and Ramesh S.S. Tetrahedron Lett. 45 (2004) 1985
54. Mehta G., and Islam K. Tetrahedron Lett. 45 (2004) 7683
55. Crystallographic data (excluding structure factors) for the structure in this paper has been deposited at the Cambridge Crystallographic Data Centre as supplementary publication. CCDC no. 247818. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
56. The optical rotation of monomer 15 was not obtained. The (+) and (-) notation has therefore been arbitrarily assigned for our discussion.
57. All calculations were performed using:. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery Jr. J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B.G., Chen W., Wong M.W., Andres J.L., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98 (Revision A.7) (1998), Gaussian, Pittsburgh, PA
58. Kohrt J.T., Gu J.-X., and Johnson C.R. J. Org. Chem. 63 (1998) 5088