Total synthesis of strobilurin B using a hetero-bis-metallated pentadiene linchpin

Chemical Communications

Volumn , Issue 4, 2006, Pages 423-425

  Coleman, Robert S ^a   Lu, Xiaoling ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ANTIFUNGAL AGENT; DEMOXYTOCIN; STROBILURIN B; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COVALENT BOND; HYDROBORATION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; STILLE REACTION; STRUCTURE ANALYSIS; SUZUKI REACTION; SYNTHESIS;

EID: 33645454831     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b514233d     Document Type: Article

References (37)

1. H. Sauter W. Steglich T. Anke Angew. Chem., Int. Ed. 1999 38 1328
2. T. Anke H. J. Hecht G. Schramm W. Steglich J. Antibiot. 1979 32 1112
3. P. Kraiczy U. Haase S. Gencic S. Flindt T. Anke U. Brandt G. Von Jagow Eur. J. Biochem./FEBS 1996 235 54
4. K. Beautement J. M. Clough Tetrahedron Lett. 1987 28 475
5. G. Bertram A. Scherer W. Steglich W. Weber Tetrahedron Lett. 1996 37 7955
6. S. Kroiss W. Steglich Tetrahedron 2004 60 4921
7. M. Sutter Tetrahedron Lett. 1989 30 5417
8. D. M. Hodgson J. Witherington B. A. Moloney L. C. Richards J. L. Brayer Synlett 1995 32
9. R. Rossi F. Bellina A. Carpita Synlett 1996 356
10. D. Milstein J. K. Stille J. Am. Chem. Soc. 1978 100 3636
11. J. K. Stille Angew. Chem., Int. Ed. Engl. 1986 25 508
12. V. Farina Pure Appl. Chem. 1996 68 73
13. V. Farina V. Krishnamurthy W. J. Scott Org. React. 1997 50 1
14. N. Miyaura A. Suzuki Chem. Rev. 1995 95 2457
15. S. P. Stanforth Tetrahedron 1998 54 263
16. A. Suzuki J. Organomet. Chem. 1999 576 147
17. R. S. Coleman M. C. Walczak E. L. Campbell J. Am. Chem. Soc. 2005 127 16038
18. R. S. Coleman M. C. Walczak Org. Lett. 2005 7 2289
19. M. Havranek D. Dvorak Synthesis 1998 1264
20. B. Dominguez Y. Pazos A. R. de Lera J. Org. Chem. 2000 65 5917
21. K. Takai N. Shinomiya H. Kaihara N. Yoshida T. Moriwake K. Utimoto Synlett 1995 963
22. P. G. M. Wuts P. A. Thompson J. Organomet. Chem. 1982 234 137
23. C. E. Castro W. C. Kray, Jr. J. Am. Chem. Soc. 1966 88 4447
24. J. K. Kochi P. E. Mocadlo J. Am. Chem. Soc. 1966 88 4094
25. J. K. Kochi J. W. Powers J. Am. Chem. Soc. 1970 92 137
26. I. Beletskaya C. Moberg Chem. Rev. 1999 99 3435
27. A. B. Smith III S. M. Condon J. A. McCauley J. L. Leazer, Jr. J. W. Leahy R. E. Maleczka J. Am. Chem. Soc. 1997 119 962
28. A. V. Kalinin S. Scherer V. Snieckus Angew. Chem., Int. Ed. 2003 42 3399
29. 4Pd, CuTC, DMF
30. A. F. Littke C. Dai G. C. Fu J. Am. Chem. Soc. 2000 122 4020
31. A. F. Littke L. Schwarz G. C. Fu J. Am. Chem. Soc. 2002 124 6343
32. K. Itami T. Kamei J. Yoshida J. Am. Chem. Soc. 2003 125 14670
33. (aq), 0°C) and reaction of the aryl diazonium intermediate with KI
34. 3, toluene/EtOH
35. T. Anke F. Oberwinkler W. Steglich G. Schramm J. Antibiot. 1977 30 806
36. G. Schramm W. Steglich T. Anke F. Oberwinkler Chem. Ber. 1978 111 2779
37. T. Anke G. Schramm B. Schwalge B. Steffan W. Steglich Liebigs Ann. Chem. 1984 1616