Synthesis of C-glycosyl lactones and protected C-glycosyl amino acids: Use of radical cyclization

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 770-779

  Zhang, Junhu ^a   Clive, Derrick L J ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

(2,2 DIPHENYLHYDRAZONE)ACETIC ACID; AMINO ACID DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTALLIZATION; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; ESTERIFICATION;

EID: 0033525179     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981435w     Document Type: Article

References (43)

1. Barber, H. J.; Lunt, E. J. Chem. Soc. 1965, 1468-1473.
2. Clive, D. L. J.; Zhang, J. Chem. Commun. 1997, 549.
3. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
4. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
5. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
6. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
7. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
8. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
9. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
10. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
11. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
12. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
13. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
14. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
15. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897- 9898.
16. For leading references to other preparations of C-glycosyl amino acids, see, for example: (a) Dondoni, A.; Junquera, F.; Merchán, F. L.; Merino, P.; Scherrmann, M.-C.; Tejero, T. J. Org. Chem. 1997, 62, 5484-5496. Recent examples of the synthesis of C-glycosyl amino acids or peptides: (b) Czernecki, S.; Horns, S.; Valery, J.-M. J. Org. Chem. 1995, 60, 650-655. (c) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (d) Coutrot, P.; Grison, C.; Coutrot, F. Synlett 1998, 393-395. (e) Tedebark, U.; Meldal, M.; Panza, L.; Bock, K. Tetrahedron Lett. 1998, 39, 1815-1818. (f) Hoffmann, M.; Burkhart, F.; Hessler, G.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. (g) Raasu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1995, 6, 371-374. (h) Petruš, L.; BeMillar, J. N. Carbohydr. Res. 1992, 230, 197-200. (i) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (j) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904. (k) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897-3900. (l) Pochet, S.; Allard, P.; Huynh-Dinh, T.; Igolen, J. J. Carbohydr. Chem. 1982-3, 1, 277-288. (m) Bischofberger, K.; Brink, A. J.; de Villiers, O. G.; Hall, R. H. J. Chem. Soc., Perkin Trans I 1977, 1472-1476. (n) Cf. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898.
17. For examples of recent synthetic work related to such antibiotics, see: (a) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (b) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853-3857. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787.
18. For examples of recent synthetic work related to such antibiotics, see: (a) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (b) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853-3857. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787.
19. For examples of recent synthetic work related to such antibiotics, see: (a) Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755-759. (b) Barrett, A. G. M.; Lebold, S. A. J. Org. Chem. 1990, 55, 3853-3857. (c) Garner, P.; Park, J. M. J. Org. Chem. 1990, 55, 3772-3787.
20. Review on glycobiology: Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
21. Cf. McDevitt, J. P.; Lansbury, P. T., Jr. J. Am. Chem. Soc. 1996, 118, 3818-3828.
22. Giese, B.; Gilges, S.; Gröninger, K. S.; Lamberth, C.; Witzel, T. Justus Liebigs Ann. Chem. 1988, 615-617.
23. A mixture of both anomers is formed by using PhSeSePh/Zn-AcOH (Fourrey, J.-L.; Henry, G.; Jouin, P. Tetrahedron Lett. 1980, 455-458).
24. Backinowsky, L. V.; Nepogod'ev, S. A.; Shashkov, A. S.; Kochetkov, N. K Carbohydr. Res. 1985, 138, 41-54.
25. Du, Y.; Kong, F. J. Carbohydr. Chem. 1996, 15, 797-817.
26. Schmidt, O. Th. In Methods in Carbohydrate Chemistry; Whistler, R. L., Wolfrom, M. L., Eds.; Academic Press: London, 1963; Vol. 2, p 322.
27. Cf. Kuszmann, J.; Sohár, P.; Kiss, L. Carbohydr. Res. 1978, 63, 115-125.
28. de Jong, E. G.; Heerma, W.; Dujardin, B.; Haverkamp, J.; Vliegenthart, J. F. G. Carbohydr. Res. 1978, 60, 229-239.
29. Nayak, U. G.; Whistler, R. L. J. Org. Chem. 1969, 34, 97-100.
30. Knapp, S.; Naughton, A. B. J.; Jaramillo, C.; Pipik, B. J. Org. Chem. 1992, 57, 7328-7334.
31. Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinay, P. Synlett 1993, 522-524.
32. The procedures are outlined in the Supporting Information. (18) Beckwith, A. L. J.; Crich, D.; Duggan, P. J.; Yao, Q. Chem. Rev. 1997, 97, 3273-3313.
33. Giese, B.; Gröninger, K. S. Org. Synth. 1990, 69, 66-71.
34. Sturino, C. F.; Fallis, A. G. J. Org. Chem. 1994, 59, 6514-6516.
35. For an example of rearrangement before closure, see ref 2.
36. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994; p 618.
37. 13C NMR spectrum of the crude reaction product from an attempted radical cyclization of 26 showed signals at δ 172.9, 163.7, and 101.0, suggesting the presence of a γ-lactone (δ 163.7) resulting from acyl migration and cyclization [C(I) OCHO], as well as simple reduction product or starting material (δ 172.9).
38. (a) Beckwith, A. L. J.; Phillipou, G.; Serelis, A. K. Tetrahedron Lett. 1981, 22, 2811-2814.
39. (b) Clive, D. L. J.; Joussef, A. C. J. Chem. Soc., Perkin Trans, 1 1991, 2797-2799 and references therein.
40. J. Zhang, unpublished observations.
41. Cf.: Verdegaal, C. H. M.; Jansse, P. L.; de Rooij, J. F. M.; van Boom, J. H. Tetrahedron Lett. 1980, 1571-1574.
42. Burke, M. J.; Allen, J. G. J. Org. Chem. 1997, 62, 7054-7057.
43. Clive, D. L. J.; Wickens, P. L.; Sgarbi, P. W. M. J. Org. Chem. 1996, 61, 7426-7437.