Synthesis of C(3) benzofuran-derived bisaryl quaternary centers: Approaches to diazonamide A

Organic Letters

Volumn 2, Issue 22, 2000, Pages 3521-3523

  Fuerst, Douglas E ^a   Stoltz, Brian M ^a,b   Wood, John L ^a  

^a YALE UNIVERSITY   (United States)

^b California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DIAZONAMIDE A; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FUSED HETEROCYCLIC RINGS; OXAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OXAZOLES; STEREOISOMERISM;

EID: 0034597507     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006578v     Document Type: Article

References (24)

1. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303.
2. (a) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem 1994, 66, 2107.
3. (b) Konopelski, J. P.; Hottenroth, J. M.; Altra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609.
4. (c) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413.
5. (d) Jamison, T. F. Ph.D. Dissertation, Harvard University, Cambridge, MA, 1997.
6. (e) Boto, A.; Ling M.; Meek, G.; Pattenden, G. Tetrahedron Lett. 1998, 39, 2223.
7. (f) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223.
8. (g) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640.
9. (h) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398.
10. (i) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451.
11. (j) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831.
12. (k) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835.
13. (l) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937.
14. (m) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031.
15. (n) Vedejs, E.; Barda, D. A. Org. Lett. 2000, 2, 1033.
16. 13C spectra, as well as appropiate parent ion identification by high-resolution mass spectrometry.
17. White, W. N.; Fife, W. K. J. Am. Chem. Soc. 1961, 83, 3846.
18. Padwa, A.; Wisnieff, T. J.; Walsh, E. J. J. Org. Chem. 1989, 54, 299.
19. Ouihia, A.; Rene, L.; Guilhelm, J.; Pascard, C.; Badet, B. J. Org. Chem. 1993, 58, 1641.
20. A second compound that appears to be the product of aryl C-H insertion can also be isolated from the reaction mixture in 15% yield.
21. Cyclopropane 20 can also be opened under acidic conditions (p-TsOH, 1 equiv) to give a 2:1 mixture of i and ii, respectively. (Equation Presented)
22. 2O. The formation and conversion of 21 can also be monitored by TLC analysis of the reaction mixture. (Equation Presented)
23. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
24. 3. At this time the absolute stereochemistry of 20 is not known; 20 is only drawn as shown for illustrative purposes. For further details see the Supporting Information.