Studies directed toward the synthesis of the scabrosins: validation of a tandem enyne metathesis approach

Tetrahedron

Volumn 62, Issue 45, 2006, Pages 10528-10540

  Middleton, Mark D ^a   Peppers, Brian P ^a   Diver, Steven T ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

1,3 Cyclohexadienes; B ckvall reaction; Enyne metathesis; Epidithiadiketopiperazine; Grubbs' catalyst; Hoveyda catalyst; Scabrosin; Tandem metathesis

Indexed keywords

ALKYNE DERIVATIVE; AMIDE; AMINO ACID; ANTIBIOTIC AGENT; CARBENE; EMBEWELAMIDE A; EMBEWELAMIDE B; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; PALLADIUM; PIPERAZINEDIONE; RUTHENIUM; SCABROSIN A; SCABROSIN B; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHIRALITY; COMPARATIVE STUDY; CYCLIZATION; DRUG ISOLATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; LABORATORY; METHODOLOGY; PRIORITY JOURNAL; RING CLOSING METATHESIS; STEREOCHEMISTRY; VALIDATION PROCESS;

EID: 33748978228     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.089     Document Type: Article

References (50)

1. Williams D.E., Bombuwala K., Lobkovsky E., De Silva E.D., Veranja K., Allen T.M., Clardy J., and Andersen R.J. Tetrahedron Lett. 39 (1998) 9579-9582
2. Nagarajan R., Huckstep L.L., Lively D.H., DeLong D.C., Marsh M.M., and Neuss N. J. Am. Chem. Soc. 90 (1968) 2980-2982
3. Neuss N., Nagarajan R., Molloy B.B., and Huckstep L.L. Tetrahedron Lett. (1968) 4467-4471
4. Nagarajan R., Neuss N., and Marsh M.M. J. Am. Chem. Soc. 90 (1968) 6518-6519
5. Kleinwachter P., Dahse H.-M., Luhmann U., Schlegel B., and Dornberger K. J. Antibiot. 54 (2001) 521-525
6. Tan R.X., Jensen P.R., Williams P.G., and Fenical W. J. Nat. Prod. 67 (2004) 1374-1382
7. Fukuyama T., and Kishi Y. J. Am. Chem. Soc. 98 (1976) 6723-6724
8. Fukuyama T., Nakatsuka S., and Kishi Y. Tetrahedron 37 (1981) 2045-2078
9. Murdock K.C. J. Med. Chem. 17 (1974) 827-835
10. Ho P.P.K., and Walters C.P. Ann. N.Y. Acad. Sci. 173 (1970) 438-443
11. Ottenheijm H.C.J., Herscheid J.D.M., Tijhuis M.W., Nivard R.J.F., De Clercq E., and Prick P.A.J. J. Med. Chem. 21 (1978) 799-804
12. Ottenheijm H.C.J., Herscheid J.D.M., Tijhuis M.W., Oosterbaan M., and De Clercq E. J. Med. Chem. 21 (1978) 796-799
13. Ottenheijm H.C.J. Chem. Ber. 111 (1978) 2064-2065
14. Chai C.L.L., Elix J.A., Huleatt P.B., and Waring P. Bioorg. Med. Chem. 12 (2004) 5991-5995
15. Ernst-Russel M.A., Chai C.L.L., Hurne A.M., Waring P., Hockless D.C.R., and Elix J.A. Aust. J. Chem. 52 (1999) 279-283
16. Mori M. Ene-Yne Metathesis. In: Grubbs R.H. (Ed). Handbook of Metathesis Vol. 2 (2003), Wiley-VCH, Weinheim 176-204
17. Poulsen C.S., and Madsen R. Synthesis (2003) 1-18
18. Diver S.T., and Giessert A.J. Chem. Rev. 104 (2004) 1317-1382
19. Stragies R., Schuster M., and Blechert S. Angew. Chem., Int. Ed. 36 (1997) 2518-2520
20. Galan B.R., Giessert A.J., Keister J.B., and Diver S.T. J. Am. Chem. Soc. 127 (2005) 5762-5763
21. Smulik J.A., and Diver S.T. Tetrahedron Lett. 42 (2001) 171-174
22. Kulkarni A.A., and Diver S.T. Org. Lett. 5 (2003) 3463-3466
23. Kulkarni A.A., and Diver S.T. J. Am. Chem. Soc. 126 (2004) 8110-8111
24. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360-11370
25. Middleton M.D., and Diver S.T. Tetrahedron Lett. 46 (2005) 4039-4043
26. O'Donnell M.J. Acc. Chem. Res. 37 (2004) 506-517
27. O'Donnell M.J., and Delgado F. Tetrahedron 57 (2001) 6641-6650
28. Ooi T., and Maruoka K. Acc. Chem. Res. 37 (2004) 526-533
29. Ooi T., Kameda M., and Maruoka K. J. Am. Chem. Soc. 121 (1999) 6519-6520
30. Lygo B., and Humphreys L.D. Tetrahedron Lett. 43 (2002) 6677-6679
31. Park H.-g., Jeong B.-S., Yoo M.-S., Lee J.-H., Park M.-k., Lee Y.-J., Kim M.-J., and Jew S.-s. Angew. Chem., Int. Ed. 41 (2002) 3036-3038
32. Jew S.-s., Jeong B.-S., Yoo M.-S., Huh H., and Park H.-g. Chem. Commun. (Cambridge) (2001) 1244-1245
33. Corey E.J., Xu F., and Noe M.C. J. Am. Chem. Soc. 119 (1997) 12414-12415
34. Okino T., and Takemoto Y. Org. Lett. 3 (2001) 1515-1517
35. Previously, we have shown that we can decrease catalyst loadings on scale-up.
36. Rodriguez-Conesa S., Candal P., Jimenez C., and Rodriguez J. Tetrahedron Lett. 42 (2001) 6699-6702
37. We have shown that the methylene-free metathesis is a scaleable procedure. See: Kulkarni, A. A.; Diver, S. T. Org. Synth., in press.
38. Ahn Y.M., Yang K., and Georg G.I. Org. Lett. 3 (2001) 1411-1413
39. While this manuscript was under review, we found that lower catalyst loadings can be used at higher concentrations of 1,5-cyclooctadiene. For the same substrate in Eq. 5, we utilized 7.5 mol % ruthenium carbene catalyst and 9 equiv COD to obtain an 80% isolated yield of cyclohexadiene product 14. See:. Peppers B.P., Kulkarni A.A., and Diver S.T. Org. Lett. 8 (2006) 2539-2542
40. Bäckvall J.-E. In: Stang P.J., and Diedrich F. (Eds). Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, Weinheim 339-385
41. Andersson P.G., and Bäckvall J.-E. In: Negishi E.-i. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 (2002), Wiley, Hoboken, NJ 1859-1874
42. Bäckvall J.E., and Andersson P.G. J. Am. Chem. Soc. 112 (1990) 3683-3685
43. Bäckvall J.E., and Andersson P.G. J. Am. Chem. Soc. 114 (1992) 6374-6381
44. Bäckvall J.E., Nystroem J.E., and Nordberg R.E. J. Am. Chem. Soc. 107 (1985) 3676-3686
45. Bäckvall J.E., Nordberg R.E., and Nystroem J.E. Tetrahedron Lett. 23 (1982) 1617-1620
46. Bäckvall J.E., and Vaagberg J.O. Org. Synth. 69 (1990) 38-43
47. Banker R., and Carmeli S. Tetrahedron 55 (1999) 10835-10844
48. Tung R.D., Dhaon M.K., and Rich D.H. J. Org. Chem. 51 (1986) 3350-3354
49. Tung R.D., and Rich D.H. J. Am. Chem. Soc. 107 (1985) 4342-4343
50. The Schlenk flask is fitted with a rubber septum on the sidearm. This septum accommodates the argon line and the needle from the syringe pump.