Chiral auxiliary based approach toward the synthesis of C-glycosylated amino acids

Organic Letters

Volumn 3, Issue 9, 2001, Pages 1375-1377

  Westermann, Bernhard ^a   Walter, Armin ^a   Flörke, Ulrich ^a   Altenbach, Hans Josef ^b  

^a UNIVERSITY OF PADERBORN   (Germany)

^b UNIVERSITY OF WUPPERTAL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; GLYCINE; GLYCOSIDE; MENTHOL; MENTHONE; TERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ELLIPTOCYTOSIS; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINO ACIDS; CYCLIZATION; ELLIPTOCYTOSIS, HEREDITARY; GLYCINE; GLYCOSIDES; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; MENTHOL; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TERPENES;

EID: 0035799866     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015743j     Document Type: Article

References (49)

1. Reviews and concepts: Seitz, O. ChemBioChem 2000, 1, 214-246. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4494. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4538. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. Sears, P.; Wong, C. H. Angew. Chem. 1999, 111, 2446-2471; Ange Chem., Int. Ed. 1999, 38, 2300-2324. Davis, B. G. J. Chem. Soc., Perkin Trans. I 1999, 3215-3237. Warren, D. G.; Garg, H. G. In Glycopeptides and Related Compounds; Warren, C. D., Large, D. G., Eds.: Marcel Dekker: New York, 1997. Bill, R. M.; Putsch, S. L. Chem. Biol. 1996, 3, 145-149.
2. Reviews and concepts: Seitz, O. ChemBioChem 2000, 1, 214-246. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4494. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4538. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. Sears, P.; Wong, C. H. Angew. Chem. 1999, 111, 2446-2471; Ange Chem., Int. Ed. 1999, 38, 2300-2324. Davis, B. G. J. Chem. Soc., Perkin Trans. I 1999, 3215-3237. Warren, D. G.; Garg, H. G. In Glycopeptides and Related Compounds; Warren, C. D., Large, D. G., Eds.: Marcel Dekker: New York, 1997. Bill, R. M.; Putsch, S. L. Chem. Biol. 1996, 3, 145-149.
3. Reviews and concepts: Seitz, O. ChemBioChem 2000, 1, 214-246. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4494. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4538. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. Sears, P.; Wong, C. H. Angew. Chem. 1999, 111, 2446-2471; Ange Chem., Int. Ed. 1999, 38, 2300-2324. Davis, B. G. J. Chem. Soc., Perkin Trans. I 1999, 3215-3237. Warren, D. G.; Garg, H. G. In Glycopeptides and Related Compounds; Warren, C. D., Large, D. G., Eds.: Marcel Dekker: New York, 1997. Bill, R. M.; Putsch, S. L. Chem. Biol. 1996, 3, 145-149.
4. Reviews and concepts: Seitz, O. ChemBioChem 2000, 1, 214-246. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4494. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4538. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. Sears, P.; Wong, C. H. Angew. Chem. 1999, 111, 2446-2471; Ange Chem., Int. Ed. 1999, 38, 2300-2324. Davis, B. G. J. Chem. Soc., Perkin Trans. I 1999, 3215-3237. Warren, D. G.; Garg, H. G. In Glycopeptides and Related Compounds; Warren, C. D., Large, D. G., Eds.: Marcel Dekker: New York, 1997. Bill, R. M.; Putsch, S. L. Chem. Biol. 1996, 3, 145-149.
5. Reviews and concepts: Seitz, O. ChemBioChem 2000, 1, 214-246. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4494. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4538. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. Sears, P.; Wong, C. H. Angew. Chem. 1999, 111, 2446-2471; Ange Chem., Int. Ed. 1999, 38, 2300-2324. Davis, B. G. J. Chem. Soc., Perkin Trans. I 1999, 3215-3237. Warren, D. G.; Garg, H. G. In Glycopeptides and Related Compounds; Warren, C. D., Large, D. G., Eds.: Marcel Dekker: New York, 1997. Bill, R. M.; Putsch, S. L. Chem. Biol. 1996, 3, 145-149.
6. Reviews and concepts: Seitz, O. ChemBioChem 2000, 1, 214-246. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4494. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4538. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. Sears, P.; Wong, C. H. Angew. Chem. 1999, 111, 2446-2471; Ange Chem., Int. Ed. 1999, 38, 2300-2324. Davis, B. G. J. Chem. Soc., Perkin Trans. I 1999, 3215-3237. Warren, D. G.; Garg, H. G. In Glycopeptides and Related Compounds; Warren, C. D., Large, D. G., Eds.: Marcel Dekker: New York, 1997. Bill, R. M.; Putsch, S. L. Chem. Biol. 1996, 3, 145-149.
7. Reviews and concepts: Seitz, O. ChemBioChem 2000, 1, 214-246. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4494. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4538. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. Sears, P.; Wong, C. H. Angew. Chem. 1999, 111, 2446-2471; Ange Chem., Int. Ed. 1999, 38, 2300-2324. Davis, B. G. J. Chem. Soc., Perkin Trans. I 1999, 3215-3237. Warren, D. G.; Garg, H. G. In Glycopeptides and Related Compounds; Warren, C. D., Large, D. G., Eds.: Marcel Dekker: New York, 1997. Bill, R. M.; Putsch, S. L. Chem. Biol. 1996, 3, 145-149.
8. Reviews and concepts: Seitz, O. ChemBioChem 2000, 1, 214-246. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4494. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4538. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. Sears, P.; Wong, C. H. Angew. Chem. 1999, 111, 2446-2471; Ange Chem., Int. Ed. 1999, 38, 2300-2324. Davis, B. G. J. Chem. Soc., Perkin Trans. I 1999, 3215-3237. Warren, D. G.; Garg, H. G. In Glycopeptides and Related Compounds; Warren, C. D., Large, D. G., Eds.: Marcel Dekker: New York, 1997. Bill, R. M.; Putsch, S. L. Chem. Biol. 1996, 3, 145-149.
9. Reviews and concepts: Seitz, O. ChemBioChem 2000, 1, 214-246. Koeller, K. M.; Wong, C. H. Chem. Rev. 2000, 100, 4465-4494. Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4538. Marcaurelle, L. A.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390. Sears, P.; Wong, C. H. Angew. Chem. 1999, 111, 2446-2471; Ange Chem., Int. Ed. 1999, 38, 2300-2324. Davis, B. G. J. Chem. Soc., Perkin Trans. I 1999, 3215-3237. Warren, D. G.; Garg, H. G. In Glycopeptides and Related Compounds; Warren, C. D., Large, D. G., Eds.: Marcel Dekker: New York, 1997. Bill, R. M.; Putsch, S. L. Chem. Biol. 1996, 3, 145-149.
10. Dondoni, A,; Marra. A.; Massi, A. J. Org. Chem. 1999, 64, 933-944. Hoffmann, M.; Burkhart, F.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. Dechantsreiter, M. A.; Burkhart, F.; Kessler, H. Tetrahedron Lett. 1998, 39, 253-254. Kim, J. M.; Roy, R. Tetrahedron Lett. 1997, 38, 3487-3490 and references therein.
11. Dondoni, A,; Marra. A.; Massi, A. J. Org. Chem. 1999, 64, 933-944. Hoffmann, M.; Burkhart, F.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. Dechantsreiter, M. A.; Burkhart, F.; Kessler, H. Tetrahedron Lett. 1998, 39, 253-254. Kim, J. M.; Roy, R. Tetrahedron Lett. 1997, 38, 3487-3490 and references therein.
12. Dondoni, A,; Marra. A.; Massi, A. J. Org. Chem. 1999, 64, 933-944. Hoffmann, M.; Burkhart, F.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. Dechantsreiter, M. A.; Burkhart, F.; Kessler, H. Tetrahedron Lett. 1998, 39, 253-254. Kim, J. M.; Roy, R. Tetrahedron Lett. 1997, 38, 3487-3490 and references therein.
13. Dondoni, A,; Marra. A.; Massi, A. J. Org. Chem. 1999, 64, 933-944. Hoffmann, M.; Burkhart, F.; Kessler, H. Helv. Chim. Acta 1996, 79, 1519-1532. Dechantsreiter, M. A.; Burkhart, F.; Kessler, H. Tetrahedron Lett. 1998, 39, 253-254. Kim, J. M.; Roy, R. Tetrahedron Lett. 1997, 38, 3487-3490 and references therein.
14. Walter, A.; Westermann, B. Synlett 2000, 1682-1684. Westermann, B.; Walter, A.; Diedrichs, N. Angew. Chem. 1999, 111, 3554-3556; Angew. Chem., Int. Ed. 1999, 38, 3384-3386. Westermann, B.; Diedrichs, N.; Gedrath, I.; Walter, A. In Bioorganic Chemistry; Diederichsen, U., Lindhorst, T. K., Westermann, B., Wessjohann, L. A., Eds., Wiley-VCH: Weinheim, 1999.
15. Walter, A.; Westermann, B. Synlett 2000, 1682-1684. Westermann, B.; Walter, A.; Diedrichs, N. Angew. Chem. 1999, 111, 3554-3556; Angew. Chem., Int. Ed. 1999, 38, 3384-3386. Westermann, B.; Diedrichs, N.; Gedrath, I.; Walter, A. In Bioorganic Chemistry; Diederichsen, U., Lindhorst, T. K., Westermann, B., Wessjohann, L. A., Eds., Wiley-VCH: Weinheim, 1999.
16. Walter, A.; Westermann, B. Synlett 2000, 1682-1684. Westermann, B.; Walter, A.; Diedrichs, N. Angew. Chem. 1999, 111, 3554-3556; Angew. Chem., Int. Ed. 1999, 38, 3384-3386. Westermann, B.; Diedrichs, N.; Gedrath, I.; Walter, A. In Bioorganic Chemistry; Diederichsen, U., Lindhorst, T. K., Westermann, B., Wessjohann, L. A., Eds., Wiley-VCH: Weinheim, 1999.
17. Walter, A.; Westermann, B. Synlett 2000, 1682-1684. Westermann, B.; Walter, A.; Diedrichs, N. Angew. Chem. 1999, 111, 3554-3556; Angew. Chem., Int. Ed. 1999, 38, 3384-3386. Westermann, B.; Diedrichs, N.; Gedrath, I.; Walter, A. In Bioorganic Chemistry; Diederichsen, U., Lindhorst, T. K., Westermann, B., Wessjohann, L. A., Eds., Wiley-VCH: Weinheim, 1999.
18. Reviews: Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395-4422. Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913-9959. Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
19. Reviews: Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395-4422. Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913-9959. Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
20. Reviews: Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395-4422. Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913-9959. Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
21. Reviews: Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395-4422. Du, Y.; Linhardt, R. J. Tetrahedron 1998, 54, 9913-9959. Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
22. Selected publications: Wellner, E.; Gustaffsson, T.; Bäcklund, J.; Holmdahl, R.; Kihlberg, J. ChemBioChem 2000, 1, 272-280. Vincent, S. P.; Schleyer, A.; Wong, C. H. J. Org. Chem. 2000, 65, 4440-4443. Lundquist, J. J.; Debenham, S. D.; Toone, E. J. J. Org. Chem. 2000, 65, 8245-8250. SanMartin, R.; Tavassoli, B.; Walsh, K. E. Org. Lett. 2000, 2, 4051-4054. Dominique, R.; Liu, B. C,; Das, S. K.; Roy, R. Synthesis 2000, 862-868.
23. Selected publications: Wellner, E.; Gustaffsson, T.; Bäcklund, J.; Holmdahl, R.; Kihlberg, J. ChemBioChem 2000, 1, 272-280. Vincent, S. P.; Schleyer, A.; Wong, C. H. J. Org. Chem. 2000, 65, 4440-4443. Lundquist, J. J.; Debenham, S. D.; Toone, E. J. J. Org. Chem. 2000, 65, 8245-8250. SanMartin, R.; Tavassoli, B.; Walsh, K. E. Org. Lett. 2000, 2, 4051-4054. Dominique, R.; Liu, B. C,; Das, S. K.; Roy, R. Synthesis 2000, 862-868.
24. Selected publications: Wellner, E.; Gustaffsson, T.; Bäcklund, J.; Holmdahl, R.; Kihlberg, J. ChemBioChem 2000, 1, 272-280. Vincent, S. P.; Schleyer, A.; Wong, C. H. J. Org. Chem. 2000, 65, 4440-4443. Lundquist, J. J.; Debenham, S. D.; Toone, E. J. J. Org. Chem. 2000, 65, 8245-8250. SanMartin, R.; Tavassoli, B.; Walsh, K. E. Org. Lett. 2000, 2, 4051-4054. Dominique, R.; Liu, B. C,; Das, S. K.; Roy, R. Synthesis 2000, 862-868.
25. Selected publications: Wellner, E.; Gustaffsson, T.; Bäcklund, J.; Holmdahl, R.; Kihlberg, J. ChemBioChem 2000, 1, 272-280. Vincent, S. P.; Schleyer, A.; Wong, C. H. J. Org. Chem. 2000, 65, 4440-4443. Lundquist, J. J.; Debenham, S. D.; Toone, E. J. J. Org. Chem. 2000, 65, 8245-8250. SanMartin, R.; Tavassoli, B.; Walsh, K. E. Org. Lett. 2000, 2, 4051-4054. Dominique, R.; Liu, B. C,; Das, S. K.; Roy, R. Synthesis 2000, 862-868.
26. Selected publications: Wellner, E.; Gustaffsson, T.; Bäcklund, J.; Holmdahl, R.; Kihlberg, J. ChemBioChem 2000, 1, 272-280. Vincent, S. P.; Schleyer, A.; Wong, C. H. J. Org. Chem. 2000, 65, 4440-4443. Lundquist, J. J.; Debenham, S. D.; Toone, E. J. J. Org. Chem. 2000, 65, 8245-8250. SanMartin, R.; Tavassoli, B.; Walsh, K. E. Org. Lett. 2000, 2, 4051-4054. Dominique, R.; Liu, B. C,; Das, S. K.; Roy, R. Synthesis 2000, 862-868.
27. β-2a, 6: Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4974-4978. Kraus, G. A.; Molina, M. T. J. Org. Chem. 1988, 53, 752-753. α-2b,d,e: Hosomi, A.; Sakata, Y.; Sakurai, H. Carbohydr. Res. 1987, 171, 223-232. α-2c: Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479-1482. α-2f: Horton, D. In Methods in Carbohydrate Chemistry; Whistler, R. J., BeMiller, J. N., Eds.; Academic Press: New York, 1972; Vol. 6, pp 282-285. Cui, J.; Horton, D. Carbohydr. Res. 1998, 309, 319-330.
28. β-2a, 6: Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4974-4978. Kraus, G. A.; Molina, M. T. J. Org. Chem. 1988, 53, 752-753. α-2b,d,e: Hosomi, A.; Sakata, Y.; Sakurai, H. Carbohydr. Res. 1987, 171, 223-232. α-2c: Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479-1482. α-2f: Horton, D. In Methods in Carbohydrate Chemistry; Whistler, R. J., BeMiller, J. N., Eds.; Academic Press: New York, 1972; Vol. 6, pp 282-285. Cui, J.; Horton, D. Carbohydr. Res. 1998, 309, 319-330.
29. β-2a, 6: Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4974-4978. Kraus, G. A.; Molina, M. T. J. Org. Chem. 1988, 53, 752-753. α-2b,d,e: Hosomi, A.; Sakata, Y.; Sakurai, H. Carbohydr. Res. 1987, 171, 223-232. α-2c: Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479-1482. α-2f: Horton, D. In Methods in Carbohydrate Chemistry; Whistler, R. J., BeMiller, J. N., Eds.; Academic Press: New York, 1972; Vol. 6, pp 282-285. Cui, J.; Horton, D. Carbohydr. Res. 1998, 309, 319-330.
30. β-2a, 6: Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4974-4978. Kraus, G. A.; Molina, M. T. J. Org. Chem. 1988, 53, 752-753. α-2b,d,e: Hosomi, A.; Sakata, Y.; Sakurai, H. Carbohydr. Res. 1987, 171, 223-232. α-2c: Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479-1482. α-2f: Horton, D. In Methods in Carbohydrate Chemistry; Whistler, R. J., BeMiller, J. N., Eds.; Academic Press: New York, 1972; Vol. 6, pp 282-285. Cui, J.; Horton, D. Carbohydr. Res. 1998, 309, 319-330.
31. β-2a, 6: Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4974-4978. Kraus, G. A.; Molina, M. T. J. Org. Chem. 1988, 53, 752-753. α-2b,d,e: Hosomi, A.; Sakata, Y.; Sakurai, H. Carbohydr. Res. 1987, 171, 223-232. α-2c: Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479-1482. α-2f: Horton, D. In Methods in Carbohydrate Chemistry; Whistler, R. J., BeMiller, J. N., Eds.; Academic Press: New York, 1972; Vol. 6, pp 282-285. Cui, J.; Horton, D. Carbohydr. Res. 1998, 309, 319-330.
32. β-2a, 6: Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4974-4978. Kraus, G. A.; Molina, M. T. J. Org. Chem. 1988, 53, 752-753. α-2b,d,e: Hosomi, A.; Sakata, Y.; Sakurai, H. Carbohydr. Res. 1987, 171, 223-232. α-2c: Giannis, A.; Sandhoff, K. Tetrahedron Lett. 1985, 26, 1479-1482. α-2f: Horton, D. In Methods in Carbohydrate Chemistry; Whistler, R. J., BeMiller, J. N., Eds.; Academic Press: New York, 1972; Vol. 6, pp 282-285. Cui, J.; Horton, D. Carbohydr. Res. 1998, 309, 319-330.
33. Vogt, A.; Altenbach, H.-J.; Kirschbaum, M.; Hahn, M. G.; Matthäus, M. S. P.; Herrmann, A. R. EP 976721, 2000; Chem. Abstr. 2000, 132, 108296. Altenbach, H.-J.; Hahn, M.; Matthäus, M. S. P. N,N-Acetals from Menthone with α-Aminocarboxylic acid and N-Methylamides. 12th International Conference on Organic Synthesis, Venice, Italy, 1998, OC-68.
34. Vogt, A.; Altenbach, H.-J.; Kirschbaum, M.; Hahn, M. G.; Matthäus, M. S. P.; Herrmann, A. R. EP 976721, 2000; Chem. Abstr. 2000, 132, 108296. Altenbach, H.-J.; Hahn, M.; Matthäus, M. S. P. N,N-Acetals from Menthone with α-Aminocarboxylic acid and N-Methylamides. 12th International Conference on Organic Synthesis, Venice, Italy, 1998, OC-68.
35. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98. 863-909. Torssell, K. B. G. Nitrite Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: Weinheim, 1988. Little, R. D. Thermal Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991, Vol. 5.
36. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98. 863-909. Torssell, K. B. G. Nitrite Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: Weinheim, 1988. Little, R. D. Thermal Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991, Vol. 5.
37. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98. 863-909. Torssell, K. B. G. Nitrite Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: Weinheim, 1988. Little, R. D. Thermal Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: New York, 1991, Vol. 5.
38. Selected publications: Cardona, F.; Valenzy, S.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 1999, 1319-1323. Cardona, F.; Valenza, S.; Picasso, S. Goti, A.; Brandi, A. J. Org. Chem. 1998, 63, 7311-7318. Tamura, O.; Kuraki, T; Sakai, Y.; Takizawa. J. I.; Yoshino, J.; Monta, Y.; Mita, N.: Gotanda, K.; Sakamoto, M. Tetrahedron Lett. 1999, 40, 895-898. Baldwin, S. W.; Young, B. G.; McPhail, A. T. Tetrahedron Lett. 1998, 39, 6819-6822. Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746.
39. Selected publications: Cardona, F.; Valenzy, S.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 1999, 1319-1323. Cardona, F.; Valenza, S.; Picasso, S. Goti, A.; Brandi, A. J. Org. Chem. 1998, 63, 7311-7318. Tamura, O.; Kuraki, T; Sakai, Y.; Takizawa. J. I.; Yoshino, J.; Monta, Y.; Mita, N.: Gotanda, K.; Sakamoto, M. Tetrahedron Lett. 1999, 40, 895-898. Baldwin, S. W.; Young, B. G.; McPhail, A. T. Tetrahedron Lett. 1998, 39, 6819-6822. Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746.
40. Selected publications: Cardona, F.; Valenzy, S.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 1999, 1319-1323. Cardona, F.; Valenza, S.; Picasso, S. Goti, A.; Brandi, A. J. Org. Chem. 1998, 63, 7311-7318. Tamura, O.; Kuraki, T; Sakai, Y.; Takizawa. J. I.; Yoshino, J.; Monta, Y.; Mita, N.: Gotanda, K.; Sakamoto, M. Tetrahedron Lett. 1999, 40, 895-898. Baldwin, S. W.; Young, B. G.; McPhail, A. T. Tetrahedron Lett. 1998, 39, 6819-6822. Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746.
41. Selected publications: Cardona, F.; Valenzy, S.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 1999, 1319-1323. Cardona, F.; Valenza, S.; Picasso, S. Goti, A.; Brandi, A. J. Org. Chem. 1998, 63, 7311-7318. Tamura, O.; Kuraki, T; Sakai, Y.; Takizawa. J. I.; Yoshino, J.; Monta, Y.; Mita, N.: Gotanda, K.; Sakamoto, M. Tetrahedron Lett. 1999, 40, 895-898. Baldwin, S. W.; Young, B. G.; McPhail, A. T. Tetrahedron Lett. 1998, 39, 6819-6822. Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746.
42. Selected publications: Cardona, F.; Valenzy, S.; Goti, A.; Brandi, A. Eur. J. Org. Chem. 1999, 1319-1323. Cardona, F.; Valenza, S.; Picasso, S. Goti, A.; Brandi, A. J. Org. Chem. 1998, 63, 7311-7318. Tamura, O.; Kuraki, T; Sakai, Y.; Takizawa. J. I.; Yoshino, J.; Monta, Y.; Mita, N.: Gotanda, K.; Sakamoto, M. Tetrahedron Lett. 1999, 40, 895-898. Baldwin, S. W.; Young, B. G.; McPhail, A. T. Tetrahedron Lett. 1998, 39, 6819-6822. Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746.
43. The determined configuration is in strong correlation to previous results; see ref 9.
44. Myers, R. M.; Längsten, S. P.; Conway, S. P.; Abell, C. Org. Lett. 2000, 2, 1349-1352. Keck, G. E.; Wager, T. T.; McHardy, S. F. Tetrahedron 1999, 55, 11755-11772. Natale, N. R. Tetrahedron Lett. 1982, 23, 5009-5012.
45. Myers, R. M.; Längsten, S. P.; Conway, S. P.; Abell, C. Org. Lett. 2000, 2, 1349-1352. Keck, G. E.; Wager, T. T.; McHardy, S. F. Tetrahedron 1999, 55, 11755-11772. Natale, N. R. Tetrahedron Lett. 1982, 23, 5009-5012.
46. Myers, R. M.; Längsten, S. P.; Conway, S. P.; Abell, C. Org. Lett. 2000, 2, 1349-1352. Keck, G. E.; Wager, T. T.; McHardy, S. F. Tetrahedron 1999, 55, 11755-11772. Natale, N. R. Tetrahedron Lett. 1982, 23, 5009-5012.
47. Toshima, K.; Matsuo, G.; Ishizuka, T.; Ushiki, Y.; Nakata, M.; Matsumura, S. J. Org. Chem. 1998, 63, 2307-2313.
48. Cardona, F.; Salanski, P.; Chmielewski, M.; Valenza, S.; Goti, A.; Brandi, A. Synlett 1998, 1444-1446.
49. Bernotas, R. C.; Sabol, J. S.; Sing, L.; Friedrich, D. Synlett 1999, 653-655.