Concise Synthesis of Deacetylanisomycin and 2-Substituted Analogues from N,2-O-Dibenzyl-L-threose Imine 1

Synlett

Volumn 1996, Issue 12, 1996, Pages 1181-1183

  Veith, Ulrich ^a   Schwardt, Oliver ^a   Jäger, Volker ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

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Indexed keywords

EID: 0002217804     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5704     Document Type: Article

References (67)

1. Presented in part at the 2nd HCM Symposium "Stereoselective Organic Synthesis", Louvain-la-Neuve, 10.-12.2.1995: Poster by Veith, U.; Leurs, S.; Jäger, V.
2. (a) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 318;
3. (b) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199;
4. (c) Jäger, V.; Müller, R.; Leibold, T.; Hein, M.; Schwarz, M.; Fengler, M.; Jaroskova, L.; Pätzel, M.; LeRoy, P.-Y. Bull. Soc. Chim. Belg. 1994, 103, 491;
5. (d) Cossy, J.; Vogel, P. Studies Nat. Prod. Chem. 1993, 12, 275.
6. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
7. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
8. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
9. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
10. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
11. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
12. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
13. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
14. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
15. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
16. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
17. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
18. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
19. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
20. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
21. Anisomycin A: (a) The Merck Index, 11th ed.; Rahway: New Jersey, 1989; p. 318; (b) Schumacher, D. P.; Hall, S. S. J. Am. Chem. Soc. 1982, 104, 6076; preparation of A from carbohydrates; (c) Verheyden, J. P. H.; Richardson, A. C.; Bhatt, R. S.; Grant, B. D.; Fitch, W. L.; Moffat, J. G. Pure Appl. Chem. 1978, 50, 1363; (d) Buchanan, J. G.; MacLean, K. A.; Paulsen, H.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1985, 486; (e) Baer, H. H.; Zamkanei, M. J. Org. Chem. 1988, 53, 4786; from L-tartrate: (f) Wong, C. M.; Bucchini, J.; Chang, I.; Te Raa, J.; Schenk, R. Can. J. Chem. 1969, 47, 2421; (g) Felner, I.; Schenker, E. Helv. Chim. Acta 1970, 53, 754; (h) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51, 1069; (i) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1992, 57, 1316; (j) Kang, S. H.; Choi, H.-w. J. Chem. Soc., Chem. Commun. 1996, 1521; from amino acids; (k) Meyers, A. I.; Dupre, B. Heterocycles 1987, 25, 113; (l) Shono, T.; Kise, N. Chem. Lett. 1987, 697; (m) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419; (n) Ikota, N.; Heterocycles 1995, 41, 983; from epichlorohydrin; (o) Takano, S.; Iwabuchi, Y.; Ogasawara, K. Heterocycles 1989, 29, 1861; from divinylcarbinol via asymmetric sharpless epoxidation: (p) Shi, Z.-C.; Zeng, C.-M.; Lin, G.-Q. Heterocycles 1995, 41, 277; cf. ref. 10.
22. (a) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 1956;
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31. (a) Jäger, V.; Wehner, V. Angew. Chem. 1989, 101, 512; Angew. Chem. Int. Ed. Engl. 1989, 28, 469;
32. (b) Steuer, B.; Wehner, V.; Lieberknecht, A.; Jäger, V. Org. Synth., in print.
33. (a) Franz, T.; Hein, M.; Veith, U.; Jäger, V.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Angew. Chem. 1994, 106, 1308; Angew. Chem. Int. Ed. Engl. 1994, 33, 1298;
34. (a) Franz, T.; Hein, M.; Veith, U.; Jäger, V.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Angew. Chem. 1994, 106, 1308; Angew. Chem. Int. Ed. Engl. 1994, 33, 1298;
35. (b) Veith, U.; Leurs, S.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 329;
36. (c) Meunier, N.; Veith, U.; Jäger, V. J. Chem. Soc., Chem. Commun. 1996, 331;
37. (d) cf. Krämer, B.; Franz, T.; Jäger, V.; manuscript to be submitted.
38. 2O in pyridine; this transformation did not furnish pyrrolidine products from the aminotriols 5 in our hands); additions to a cyclic imine, see: (c) Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. Tetrahedron Lett. 1993, 34, 7213.
39. 2O in pyridine; this transformation did not furnish pyrrolidine products from the aminotriols 5 in our hands); additions to a cyclic imine, see: (c) Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. Tetrahedron Lett. 1993, 34, 7213.
40. 2O in pyridine; this transformation did not furnish pyrrolidine products from the aminotriols 5 in our hands); additions to a cyclic imine, see: (c) Horenstein, B. A.; Zabinski, R. F.; Schramm, V. L. Tetrahedron Lett. 1993, 34, 7213.
41. 2c nitroaldol addition: (a) Jäger, V.; Wehner, V. Angew. Chem. 1990, 102, 1180; Angew. Chem. Int. Ed. Engl. 1990, 29, 1169, and Pd(II)-catalyzed amidocarbonylation: (b) Jäger, V.; Hümmer, W., Angew. Chem. 1990, 102, 1182; Angew. Chem. Int. Ed. Engl. 1990, 29, 1171; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, submitted.
42. 2c nitroaldol addition: (a) Jäger, V.; Wehner, V. Angew. Chem. 1990, 102, 1180; Angew. Chem. Int. Ed. Engl. 1990, 29, 1169, and Pd(II)-catalyzed amidocarbonylation: (b) Jäger, V.; Hümmer, W., Angew. Chem. 1990, 102, 1182; Angew. Chem. Int. Ed. Engl. 1990, 29, 1171; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, submitted.
43. 2c nitroaldol addition: (a) Jäger, V.; Wehner, V. Angew. Chem. 1990, 102, 1180; Angew. Chem. Int. Ed. Engl. 1990, 29, 1169, and Pd(II)-catalyzed amidocarbonylation: (b) Jäger, V.; Hümmer, W., Angew. Chem. 1990, 102, 1182; Angew. Chem. Int. Ed. Engl. 1990, 29, 1171; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, submitted.
44. 2c nitroaldol addition: (a) Jäger, V.; Wehner, V. Angew. Chem. 1990, 102, 1180; Angew. Chem. Int. Ed. Engl. 1990, 29, 1169, and Pd(II)-catalyzed amidocarbonylation: (b) Jäger, V.; Hümmer, W., Angew. Chem. 1990, 102, 1182; Angew. Chem. Int. Ed. Engl. 1990, 29, 1171; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, submitted.
45. 2c nitroaldol addition: (a) Jäger, V.; Wehner, V. Angew. Chem. 1990, 102, 1180; Angew. Chem. Int. Ed. Engl. 1990, 29, 1169, and Pd(II)-catalyzed amidocarbonylation: (b) Jäger, V.; Hümmer, W., Angew. Chem. 1990, 102, 1182; Angew. Chem. Int. Ed. Engl. 1990, 29, 1171; Hümmer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis, submitted.
46. (a) Veith, U. Dissertation, Universität Stuttgart, 1995;
47. (b) Schwardt, O. Diplomarbeit, Universität Stuttgart, 1995;
48. (c) Schwardt, O. Dissertation, Universität Stuttgart, in preparation.
49. D = +6 (c = 0.7, MeOH)].
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