Total synthesis of hydroxystrobilurin A via Stille coupling

Tetrahedron Letters

Volumn 49, Issue 15, 2008, Pages 2414-2417

  Brooke, Darby G ^a,b   Morris, Jonathan C ^a,c  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

^c UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

FUNGICIDE; HYDROXYSTROBILURIN A; NATURAL PRODUCT; STROBILURIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STILLE REACTION;

EID: 40849126405     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.056     Document Type: Article

References (47)

1. Sauter H., Ammermann E., and Röhl F. Strobilurins-From Natural Products to a New Class of Fungicides. In: Copping L.G. (Ed). Crop Protection Agents from Nature: Natural Products and Analogues (1996), RSC, Cambridge
2. Anke T., and Steglich W. Drug Discovery from Nature. In: Grabley S., and Thiericke R. (Eds) (1999), Springer, Heidelberg
3. Daferner M., Anke T., Hellwig V., Steglich W., and Sterner O. J. Antibiot. 51 (1998) 816-822
4. Buchanan M.S., Steglich W., and Anke T.Z. Naturforsch 54c (1999) 463-468
5. Sauter H., Steglich W., and Anke T. Angew. Chem., Int. Ed. 38 (1999) 1328-1349
6. Bartlett D.W., Clough J.W., Godfrey C.R.A., Godwin J.R., Hall A.A., Heaney S.P., and Maund S.J. Pestic. Outlook 12 (2001) 143-148
7. Other natural products containing α-linked (E)-β-methoxyacrylate subunits include the oudemansins, also from Strobiluris sp. [Weber, W.; Anke, T.; Steffen, B.; Steglich, W. J. Antibiot. 1990, 43, 207-212 and Ref. 1b], some of the corynanthe alkaloids [Lounasmaa, M.; Tolvanen, A. The Corynantheine-Heteroyohimbine Group. In Chemistry of Heterocyclic Compounds; Chichester, United Kingdom, 1994; Vol. 25, pp 57-159], and the cyrmenins [Leibold, T.; Sasse, F.; Reichenbach, H.; Höfle, G. Eur. J. Org. Chem. 2004, 431-435], whilst β-linked (E)-β-methoxyacrylate, -acrylamide or -ester subunits are present in the myxothiazoles [Trowitzsch, W.; Reifenstahl, G.; Wray, V.; Gerth, K. J. Antibiot. 1980, 33, 1480-1490 and Bedorf, N.; Kunze, B.; Reichenbach, H.; Höfle, H. In Scientific Annual Report of the Gesellschaft für Biotechnologische Forschung mbH; Braunschweig, Germany, 1986; p 14], the melithioazoles/cystothiazoles [Böhlendorf, B.; Herrmann, M.; Hecht, H.-J.; Sasse, F.; Forche, E.; Kunze, B.; Reichenbach, H.; Höfle, G. Eur. J. Org. Chem. 1999, 2601-2608; Ojika, M.; Suzuki, Y.; Tsukamoto, A.; Sakagami, Y.; Fudou, R.; Yoshimura, T.; Yamanaka, S. J. Antibiot. 1998, 51, 275-281] and haliangicin [Fudou, R.; Iizuka, T.; Sato, S.; Ando, T.; Shimba, N.; Yamanaka, S. J. Antibiot. 2001, 54, 153-156].
8. Šubík J., Behúň M., and Musílek V. Biochim. Biophys. Res. Commun. 57 (1974)
9. Šubík J., Behúň M., Šmigáň P., and Musílek V. Biochim. Biophys. Acta 343 (1974) 363
10. Anke T., and Steglich W. β-Methoxyacrylate Antibiotics: From Biological Activity to Synthetic Analogues. In: Schlunegger U.P. (Ed). Biologically Active Molecules (1989), Springer, Berlin 9-25
11. Kraiczy P., Haase U., Gencic S., Flindt S., Anke T., Brandt U., and von Jagow G. Eur. J. Biochem. 235 (1996) 54-63
12. Anke T., Schramm G., Schwalge B., Steffan B.A.M., and Steglich W. Liebigs Ann. Chem. (1984) 1616-1625
13. Beautement K., and Clough J.M. Tetrahedron Lett. 28 (1987) 475-478
14. Sutter M. Tetrahedron Lett. 30 (1989) 5417-5420
15. Bertram G., Scherer A., Steglich W., Weber W., and Anke T. Tetrahedron Lett. 37 (1996) 7955-7958
16. Uchiro U., Nagasawa K., Aiba Y., and Kobayashi S. Tetrahedron Lett. 41 (2000) 4165-4168
17. Uchiro U., Nagasawa K., Aiba Y., Kotoake T., Hasegawa D., and Kobayashi S. Tetrahedron Lett. 42 (2001) 4531-4534
18. Kroiß S., and Steglich W. Tetrahedron 60 (2004) 4921-4929
19. Nicholas G.M., Blunt J.W., Cole A.L.J., and Munro M.H.G. Tetrahedron Lett. 38 (1997) 7465-7468
20. Coleman R.S., and Lu X. Chem. Commun. (2006) 423-425
21. Engler M., Anke T., Klostermeyer D., and Steglich W. J. Antibiot. 48 (1995) 884-885
22. Stille J.K., and Milstein D. J. Am. Chem. Soc. 100 (1978) 3636-3638
23. Stille J.K. Angew. Chem., Int. Ed. Engl. 25 (1986) 508
24. Farina V., Krishnamurthy V., and Scott W.J. Org. React. 50 (1997) 1
25. Stille J.K., and Labadie J.W. J. Am. Chem. Soc. 105 (1983) 6129
26. Stulgies B., Prinz P., Magull J., Rauch K., Meindl K., Ruehl S., and de Meijere A. Chem. Eur. J. 11 (2005) 308-320
27. Hosoya T., Sumi K., Doi H., Wakao M., and Suzuki M. Org. Biomol. Chem. 4 (2006) 410-415
28. Rossi R., Bellina F., and Carpita A. Synlett (1996) 356-358
29. Kim H.H., Lee C.H., Song Y.S., Park N.K., Kim B.T., and Heo J.-N. Bull. Korean Chem. Soc. 27 (2006) 191-192
30. Hodgson D.M., Witherington J., Moloney B., Richards I.C., and Brayer J.-L. Synlett (1995) 32-34
31. 4) of methyl propynoate (see Ref. 11).
32. Von Auwers K., and Müller W. Justus Liebigs Ann. Chem. 434 (1923) 165
33. Rousseau G., and Marie J.-X. Synth. Commun. 29 (1999) 3705-3710
34. Caddick S., Delisser V.M., Doyle V.E., Khan S., Avent A.G., and Vile S. Tetrahedron 55 (1999) 2737-2754
35. Such differences between reactivities of alkenyl bromides and iodides in oxidative addition processes are well-known (e.g.:. Angara G.J., Bovonsombat P., and McNelis E. Tetrahedron Lett. 33 (1992) 2285-2288
36. Several palladium/ligand catalyst and solvent combinations were tried, affording yields of 7 ranging from 48% to 66%.
37. 3, CsF, NMP.
38. Although strobilurins are known to undergo double-bond isomerization if subject to prolonged UV-irradiation [vide Refs. 1e and 4] it seems more likely that this is a palladium-mediated process:. Nakamura H., Iwama H., Ito M., and Yamamoto Y. J. Am. Chem. Soc. 121 (1999) 10850
39. Yu J., Gaunt M.J., and Spencer J.B. J. Org. Chem. 67 (2002) 4627-4629
40. This further illustrates the greater reactivity of alkenyl iodides versus bromides in oxidative additions (vide Ref. 16).
41. Auerbach J., and Weinreb S.M. J. Chem. Soc., Chem. Commun. (1974) 298-299
42. Hanessian S., Delorme D., and Dufresne Y. Tetrahedron Lett. 25 (1984) 2515-2518
43. Attempts were made to access aldehyde 19 directly, by reduction of ester 7, however these literature-based procedures:. Zakharkin L.I., and Khorlina I.M. Tetrahedron Lett. 14 (1962) 619-620
44. Szántay C., Töke L., and Kolonits P. J. Org. Chem. 31 (1996) 1447-1451 afforded trace amounts of 19, small amounts of 4, and mostly unreacted 7
45. Ley S.V., Norman J., Griffith W.P., and Marsden S.P. Synthesis (1994) 639-666
46. +).
47. Luche J.-L. J. Am. Chem. Soc. 100 (1978) 2226-2227