Asymmetrized tris(hydroxymethyl)methane as precursor of iminosugars: Application to the synthesis of isofagomine

Tetrahedron Letters

Volumn 44, Issue 2, 2003, Pages 357-360

  Guanti, Giuseppe ^a   Riva, Renata ^a  

^a UNIVERSITY OF GENOA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE INHIBITOR; IMINE; ISOFAGOMINE; METHANE; PYRIDINE DERIVATIVE; TRIS(HYDROXYMETHYL)METHANE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; ENZYMATIC DEGRADATION; EPOXIDATION; HYDROLYSIS; PRECURSOR; RING CLOSING METATHESIS; STEREOISOMERISM; STEREOSPECIFICITY; SUBSTITUTION REACTION;

EID: 0037421035     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02492-9     Document Type: Article

References (39)

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27. Several enantioselective synthesis of 28, passing through different intermediates, are known. See: (a) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778-1779; (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007-3018; (c) Kim, Y. J.; Ichikawa, M.; Ichikawa, Y. J. Org. Chem. 2000, 65, 2599-2602; (d) Pandey, G.; Kapur, M. Synthesis 2001, 1263-1267; (e) Zhao, G. H.; Deo, U. C.; Ganem, B. Org. Lett. 2001, 3, 201-203; (f) Andersch, J.; Bols, M. Chem. Eur. J. 2001, 7, 3744-3747.
28. Several enantioselective synthesis of 28, passing through different intermediates, are known. See: (a) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778-1779; (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007-3018; (c) Kim, Y. J.; Ichikawa, M.; Ichikawa, Y. J. Org. Chem. 2000, 65, 2599-2602; (d) Pandey, G.; Kapur, M. Synthesis 2001, 1263-1267; (e) Zhao, G. H.; Deo, U. C.; Ganem, B. Org. Lett. 2001, 3, 201-203; (f) Andersch, J.; Bols, M. Chem. Eur. J. 2001, 7, 3744-3747.
29. Several enantioselective synthesis of 28, passing through different intermediates, are known. See: (a) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778-1779; (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007-3018; (c) Kim, Y. J.; Ichikawa, M.; Ichikawa, Y. J. Org. Chem. 2000, 65, 2599-2602; (d) Pandey, G.; Kapur, M. Synthesis 2001, 1263-1267; (e) Zhao, G. H.; Deo, U. C.; Ganem, B. Org. Lett. 2001, 3, 201-203; (f) Andersch, J.; Bols, M. Chem. Eur. J. 2001, 7, 3744-3747.
30. Several enantioselective synthesis of 28, passing through different intermediates, are known. See: (a) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778-1779; (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007-3018; (c) Kim, Y. J.; Ichikawa, M.; Ichikawa, Y. J. Org. Chem. 2000, 65, 2599-2602; (d) Pandey, G.; Kapur, M. Synthesis 2001, 1263-1267; (e) Zhao, G. H.; Deo, U. C.; Ganem, B. Org. Lett. 2001, 3, 201-203; (f) Andersch, J.; Bols, M. Chem. Eur. J. 2001, 7, 3744-3747.
31. Several enantioselective synthesis of 28, passing through different intermediates, are known. See: (a) Jespersen, T. M.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Lundt, I.; Bols, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1778-1779; (b) Ichikawa, Y.; Igarashi, Y.; Ichikawa, M.; Suhara, Y. J. Am. Chem. Soc. 1998, 120, 3007-3018; (c) Kim, Y. J.; Ichikawa, M.; Ichikawa, Y. J. Org. Chem. 2000, 65, 2599-2602; (d) Pandey, G.; Kapur, M. Synthesis 2001, 1263-1267; (e) Zhao, G. H.; Deo, U. C.; Ganem, B. Org. Lett. 2001, 3, 201-203; (f) Andersch, J.; Bols, M. Chem. Eur. J. 2001, 7, 3744-3747.
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38. We were not able to assign the relative configuration to the prevailing isomer (which is always the same), although structures 23 and 26 seem to be the most likely.
39. 25=+22 (c 0.11, EtOH).