Amino acid based diastereoselective synthesis of elsaminose

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5743-5746

  Ruiz, María ^a   Ojea, Vicente ^a   Quintela, José Ma ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; ELSAMICIN A; ELSAMINOSE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030570886     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01173-2     Document Type: Article

References (33)

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18. 13. Cyclo[(2S)-val-gly] was obtained as described by Rose et al. Treatment of this compound with triethyloxonium tetrafluorborate allowed the preparation of the 2,5-diethoxy pyrazine derivative. See Rose, J.E., Leeson, P.D.; Gani, D. J. Chem. Soc. Perkin Trans 1 1995, 157.
19. 14. Pure aldehyde (-)-3 is elusive, probably due to hydration or polymerization.
20. 15. The excess of Schöllkopf's reagent could be recovered, and showed no racemization.
21. 16. Part of this work was presented as a poster communication to the 8th European Carbohydrate Symposium, Sevilla, Spain. 2-7 July 1995.
22. 12
23. 18. Attempts to obtain 9 by quenching the aldol reaction with methyl iodide were unsuccessful. After 24 h at rt and aqueous work-up, only traces of methylated adduct were isolated, along with the adduct 6.
24. 19. Prolonged reaction times or the use of ethers as solvent resulted in a complete hydrolysis to the corresponding 2-amino-4,5-dihydroxy acid, isolated in low yields. Lactonization of this compound was not efficiently achieved.
25. 1H NOE experiments were recorded in a BRUCKER AC200 spectrometer, using the NOEMULT.AU software for ASPECT3000 computers.
26. 0(PM3) being higher than 3 Kcal/mol). For lactones 12b and 14, rotamers (within 0.7 and 1.1 Kcal/mol of the global minimum, according to PM3 method) can better account for the observed NOEs between methyl groups and protons on C4, showed with dashed arrows in figure 2 and characteristic for the γ-lactones.
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29. 23. MNDO: Dewar, M.J.S.; Thiel, W.; J. Am. Chem. Soc. 1977, 99, 4899. AMI: Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902. PM3: Stewart, J.J.P. J. Comp. Chem. 1990, 10, 209.
30. 23. MNDO: Dewar, M.J.S.; Thiel, W.; J. Am. Chem. Soc. 1977, 99, 4899. AMI: Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902. PM3: Stewart, J.J.P. J. Comp. Chem. 1990, 10, 209.
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33. 3), 66.4 (C-4), 72.3 (C-5), 79.4 (C-3), 94.0 (C-1).