The thiazole aldehyde synthesis

Synthesis

Volumn , Issue 12, 1998, Pages 1681-1706

  Dondoni, Alessandro ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

Aldehydes; Aldol condensation; Amino ketones; Carbohydrates; Chain extention; Conjugate addition; Dipeptide isosteres; Glycosidation; Nitrones; Thiazole

Indexed keywords

AMINOKETONE; CARBOHYDRATE; THIAZOLE; THIAZOLE ALDEHYDE; UNCLASSIFIED DRUG;

AMINATION; DERIVATIZATION; DRUG SYNTHESIS; GLYCOSYLATION; HYDROLYSIS; METHYLATION; REVIEW; STRUCTURE ANALYSIS;

EID: 0032447309     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2208     Document Type: Review

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41. The following convenient abbreviations are used: 2-lithiothiazole, 2-LTT; 2-trimethylsilylthiazole, 2-TST; 2-thiazolylmethylenetriphenylphosphorane, 2-TMP; 2-thiazolylcarbonylmethylenetriphenylphosphorane, 2-TCMP; 2-acetylthiazole, 2-ATT, 2-formylthiazole, 2-FMT.
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120. Also prepared was the benzothiazole derivative (ref. 33).
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134. The unmasking and the characteristics of 78 were not reported in the original papers (ref. 35 and 81). Details can be obtained on request.
135. Dondoni, A.; Boscarato, A; Marra, A. Synlett 1993, 256.
136. For recent overviews on hetero-Diels-Alder reactions, see: Tietze, L. F.; Kettschau, G. Topics in Current Chemistry 1997, 189, 1. Tietze, L. F.; Kettschau, G.; Gewert, J. A.; Schuffenhauer, A. Current Organic Chemistry 1998, 2, 19.
137. For recent overviews on hetero-Diels-Alder reactions, see: Tietze, L. F.; Kettschau, G. Topics in Current Chemistry 1997, 189, 1. Tietze, L. F.; Kettschau, G.; Gewert, J. A.; Schuffenhauer, A. Current Organic Chemistry 1998, 2, 19.
138. Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
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140. Dondoni, A.; Marra, A. Tetrahedron Lett. 1993, 34, 7327.
141. Giörgydeák, Z.; Pelivás, I. F. Monosaccharide Sugars, Academic: London, 1998.
142. Dondoni, A.; Marra, A; Massi, A. J. Org. Chem. 1997, 62, 6261. Dondoni, A.; Marra, A; Massi, A. Carbohydr. Lett. 1997, 2, 367.
143. Dondoni, A.; Marra, A; Massi, A. J. Org. Chem. 1997, 62, 6261. Dondoni, A.; Marra, A; Massi, A. Carbohydr. Lett. 1997, 2, 367.
144. Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647.
145. Leading references to biological properties and earlier syntheses were reported in our original papers. For more recent syntheses, see: DAH: Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910. KDO: Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. KDO and DAH: López-Herrera, F. J.; Sarabia-Garcia, F. Tetrahedron Lett. 1994, 35, 6705. DAH: Davianne, G.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. J. Org. Chem. 1995, 60, 7343. KDN and Neu5Ac: Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228. KDO and KDN: Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415. Neu5Ac: Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065. KDN: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
146. Leading references to biological properties and earlier syntheses were reported in our original papers. For more recent syntheses, see: DAH: Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910. KDO: Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. KDO and DAH: López-Herrera, F. J.; Sarabia-Garcia, F. Tetrahedron Lett. 1994, 35, 6705. DAH: Davianne, G.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. J. Org. Chem. 1995, 60, 7343. KDN and Neu5Ac: Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228. KDO and KDN: Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415. Neu5Ac: Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065. KDN: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
147. Leading references to biological properties and earlier syntheses were reported in our original papers. For more recent syntheses, see: DAH: Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910. KDO: Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. KDO and DAH: López-Herrera, F. J.; Sarabia-Garcia, F. Tetrahedron Lett. 1994, 35, 6705. DAH: Davianne, G.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. J. Org. Chem. 1995, 60, 7343. KDN and Neu5Ac: Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228. KDO and KDN: Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415. Neu5Ac: Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065. KDN: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
148. Leading references to biological properties and earlier syntheses were reported in our original papers. For more recent syntheses, see: DAH: Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910. KDO: Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. KDO and DAH: López-Herrera, F. J.; Sarabia-Garcia, F. Tetrahedron Lett. 1994, 35, 6705. DAH: Davianne, G.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. J. Org. Chem. 1995, 60, 7343. KDN and Neu5Ac: Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228. KDO and KDN: Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415. Neu5Ac: Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065. KDN: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
149. Leading references to biological properties and earlier syntheses were reported in our original papers. For more recent syntheses, see: DAH: Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910. KDO: Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. KDO and DAH: López-Herrera, F. J.; Sarabia-Garcia, F. Tetrahedron Lett. 1994, 35, 6705. DAH: Davianne, G.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. J. Org. Chem. 1995, 60, 7343. KDN and Neu5Ac: Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228. KDO and KDN: Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415. Neu5Ac: Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065. KDN: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
150. Leading references to biological properties and earlier syntheses were reported in our original papers. For more recent syntheses, see: DAH: Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910. KDO: Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. KDO and DAH: López-Herrera, F. J.; Sarabia-Garcia, F. Tetrahedron Lett. 1994, 35, 6705. DAH: Davianne, G.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. J. Org. Chem. 1995, 60, 7343. KDN and Neu5Ac: Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228. KDO and KDN: Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415. Neu5Ac: Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065. KDN: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
151. Leading references to biological properties and earlier syntheses were reported in our original papers. For more recent syntheses, see: DAH: Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910. KDO: Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. KDO and DAH: López-Herrera, F. J.; Sarabia-Garcia, F. Tetrahedron Lett. 1994, 35, 6705. DAH: Davianne, G.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. J. Org. Chem. 1995, 60, 7343. KDN and Neu5Ac: Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228. KDO and KDN: Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415. Neu5Ac: Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065. KDN: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
152. Leading references to biological properties and earlier syntheses were reported in our original papers. For more recent syntheses, see: DAH: Johnson, C. R.; Kozak, J. J. Org. Chem. 1994, 59, 2910. KDO: Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714. KDO and DAH: López-Herrera, F. J.; Sarabia-Garcia, F. Tetrahedron Lett. 1994, 35, 6705. DAH: Davianne, G.; Escudier, J.-M.; Baltas, M.; Gorrichon, L. J. Org. Chem. 1995, 60, 7343. KDN and Neu5Ac: Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228. KDO and KDN: Tsukamoto, H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 6415. Neu5Ac: Takahashi, T.; Tsukamoto, H.; Kurosaki, M.; Yamada, H. Synlett 1997, 1065. KDN: Banwell, M.; De Savi, C.; Hockless, D.; Watson, K. Chem. Commun. 1998, 645.
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158. Look., G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Bols, M. Acc. Chem. Res. 1998, 31, 1. Sears, P.; Wong, C.-H. Chem. Commun. 1998, 1161.
159. Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9229. Montefiori, D. C.; Robinson, W. E., Jr.; Mitchell, W. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9248.
160. Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9229. Montefiori, D. C.; Robinson, W. E., Jr.; Mitchell, W. M. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9248.
161. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
162. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
163. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
164. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
165. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
166. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
167. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
168. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
169. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
170. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
171. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher,
172. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
173. References to biological properties and earlier syntheses were reported in our original papers. For selected recent syntheses of natural azasugars and analogues, see: Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806. Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Meyers, A. I.; Andres, C. J.; Resek, J. E.; McLaughlin, M. A.; Woodall, C. C.; Lee, P. H. J. Org. Chem. 1996, 61, 2586. Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987. Veith, U.; Schwardt, O.; Jäger, V. Synlett 1996, 1181. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295. Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. Baudat, A.; Vogel, P. J. Org. Chem. 1997, 62, 6252. Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009. Jiménez Blanco, J. L.; Díaz Pérez, V. M.; Ortiz Mellet, C.; Fuentes, J.; García Fernández, J. M.; Díaz Arribas, J. C.; Cañada, F. J. Chem. Commun. 1997, 1969. Johnson, C. R.; Johns, B. A. Tetrahedron Lett. 1997, 38, 7977. Johns, B. A.; Johnson, C. R. Tetrahedron Lett. 1998, 39, 749. Berges, D. A.; Hong, L.; Dalley, N. K. Tetrahedron 1998, 54, 5097. Kiess, F.-M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119.
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