Rhodium-catalyzed synthesis of a C(3) disubstituted oxindole: An approach to diazonamide A

Tetrahedron Letters

Volumn 44, Issue 26, 2003, Pages 4919-4921

  Sawada, Takayuki ^a   Fuerst, Douglas E ^a   Wood, John L ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; DIAZONAMIDE A; INDOLE DERIVATIVE; KETONE DERIVATIVE; OXINDOLE; RHODIUM; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CYCLOPROPANATION; RING OPENING; SYNTHESIS;

EID: 0037872649     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01038-4     Document Type: Article

References (34)

1. Lingquist N., Fenical W., Van Duyne G.D., Clardy J. J. Am. Chem. Soc. 113:1991;2303.
2. Fuerst D.E., Stoltz B.M., Wood J.L. Org. Lett. 2:2000;3521.
3. Li J., Jeong S., Esser L., Harran P.G. Angew. Chem., Int. Ed. 40:2001;4765.
4. Li J., Burgett A.W.G., Esser L., Amezcua C., Harran P.G. Angew. Chem., Int. Ed. 40:2001;4770.
5. Nicolaou K.C., Bella M., Chen D.Y.K., Huang X., Ling T., Snyder S.A. Angew. Chem., Int. Ed. 41:2002;3495.
6. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
7. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
8. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
9. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
10. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
11. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
12. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
13. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
14. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
15. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
16. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
17. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
18. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
19. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
20. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
21. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
22. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
23. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
24. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
25. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
26. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
27. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
28. For other synthetic efforts directed toward the diazonamides, see: (a) Lach, F.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6893; (b) Bagley, M. C.;. Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897; (c) Bagley, M. C.; Moody, C. J.; Pepper, A. G. Tetrahedron Lett. 2000, 41, 6901; (d) Moody, C. J.; Doyle, K. L.; Elliott, M. C.; Mowlem, T. J. J. Chem. Soc., Perkin Trans. 1 1997, 2413; (e) Moody, C. J.; Doyle, K. J.; Elliott, M. C.; Mowlem, T. J. Pure Appl. Chem. 1994, 66, 2107; (f) Hang, H. C.; Drotleff, E.; Elliott, G. I.; Ritsema, T. A.; Konopelski, J. P. Synthesis 1999, 398; (g) Konopelski, J. P.; Hottenroth, J. M.; Oltra, H. M.; Veliz, E. A.; Yang, Z. C. Synlett 1996, 609; (h) Wipf, P.; Methot, J.-L. Org. Lett. 2001, 3, 1261; (i) Wipf, P.; Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223; (j) Li, J.; Chen, X.; Burgett, A. W. G.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 2682; (k) Chen, X.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2000, 39, 937; (l) Jeong, S.; Chen, X.; Harran, P. G. J. Org. Chem. 1998, 63, 8640; (m) Kreisberg, J. D.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2001, 42, 627; (n) Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 831; (o) Chan, F.; Magnus, P.; McIver, E. G. Tetrahedron Lett. 2000, 41, 835; (p) Magnus, P.; Kreisberg, J. D. Tetrahedron Lett. 1999, 40, 451; (q) Vedejs, E.; Zajac, M. A. Org. Lett. 2001, 3, 2451; (r) Vedejs, E.; Wang, J. Org. Lett. 2000, 2, 1031; (s) Vedejs, E.; Barba, D. A. Org. Lett. 2000, 2, 1033; (t) Nicoloau, K. C.; Huang, X.; Giuseppone, N.; Bheema Rao, P.; Bella, M.; Reddy, M. V.; Snyder, S. A. Angew. Chem., Int. Ed. 2001, 40, 4705; (u) Nicolaou, K. C.; Snyder, S. A.; Simonsen, K. B.; Koumbis, A. E. Angew. Chem., Int. Ed. 2000, 39, 3473; (v) Schley, S.; Radspieler, A.; Christoph, G.; Liebscher, J. Eur. J. Org. Chem. 2002, 369; (w) Radspieler, A.; Liebscher, J. Synthesis 2001, 745.
29. For review of previous synthetic studies, see: (a) Wittmann, V. Nachr. Chem. 2002, 50, 477; (b) Ritter, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2002, 41, 2489.
30. For review of previous synthetic studies, see: (a) Wittmann, V. Nachr. Chem. 2002, 50, 477; (b) Ritter, T.; Carreira, E. M. Angew. Chem., Int. Ed. 2002, 41, 2489.
31. Figueiredo L.J.O., Kascheres C. J. Org. Chem. 62:1997;1164.
32. Although the yields of 7 obtained from successive runs were generally good (60-70%) inability to obtain analytically pure samples prevents our reporting them with certainty.
33. 6, 400 MHz): δ 0.01 (6H, s), 0.96 (9H, s), 2.16 (3H, s), 6.66 (1H, br), 7.00 (1H, d, 7 Hz), 7.20-7.28 (2H, m), 7.52 (1H, d, 7 Hz).
34. 6, 100 MHz): δ -4.20, -4.17, 18.79, 20.25, 20.51, 26.18, 79.64, 110.90, 118.45, 122.28, 122.94, 124.96, 129.59, 131.27, 131.58, 133.39, 142.22, 143.84, 152.19, 178.97.