Mitsunobu dehydration of N-Boc neomycin B

Organic and Biomolecular Chemistry

Volumn 4, Issue 1, 2006, Pages 36-37

  Quader, Sabina ^a   Boyd, Sue E ^a   Jenkins, Ian D ^a   Houston, Todd A ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; DEHYDRATION; NUCLEAR MAGNETIC RESONANCE; SUGAR (SUCROSE); TOLUENE;

DIISOPROPYL AZODICARBOXYLATE (DIAD); HEXA-N-BOC NEOMYCIN B; NOE SPECTRA; VICINAL DIOL;

CARBOXYLIC ACIDS;

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EPOXIDE; FORMIC ACID DERIVATIVE; FRAMYCETIN; T BUTYLOXYCARBONYL GROUP; T-BUTYLOXYCARBONYL GROUP; TOLUENE; WATER;

ARTICLE; CHEMISTRY; SYNTHESIS;

EPOXY COMPOUNDS; FORMIC ACID ESTERS; FRAMYCETIN; INDICATORS AND REAGENTS; TOLUENE; WATER;

EID: 33645664079     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b513113h     Document Type: Article

References (12)

1. J. D. McKinney J. E. Gomez Nat. Med. 2003 9 1356
2. S. Bottle I. D. Jenkins Chem. Commun. 1984 385
3. I. D. Jenkins M. B. Goren Chem. Phys. Lipids 1986 41 225
4. M. Fridman V. Belakhov L. V. Lee F.-S. Liang C. H. Wong T. Baasov Angew. Chem., Int. Ed. 2005 44 447
5. A. Hernandez Linares D. Fourmy J.-L. Fourrey A. Loukaci Org. Biomol. Chem. 2005 3 2064
6. S. Hanessian M. Tremblay E. E. Swayze Tetrahedron 2003 59 983
7. J. L. Asensio A. Hidalgo I. Cuesta C. Gonzalez J. Cañada C. Vicent J. L. Chiara G. Cuevas J. Jimenez-Barbero Chem. Commun. 2002 2232
8. A. C. Richardson Carbohydr. Res. 1969 10 395
9. R. D. Guthrie I. D. Jenkins Aust. J. Chem. 1981 34 1997
10. A. M. Kawamoto M. Wills J. Chem. Soc., Perkin Trans. 1 2001 1916
11. D. Ikeda Y. Horiuchi S. Kondo H. Umezawa J. Antibiot. 1980 33 1281
12. At the suggestion of both a referee and Professor Fourrey, we have repeated their experiment and isolated a compound identical by 13C-NMR to heir compound 8. However, the 1H-NMR in d5-pyridine at 90 ?C shows 6 NH peaks (compound 5, refer to the electronic supplementary information), consistent with an epoxide, but not the aziridine-azetidine structure assigned. Note added in Proof. In a personal communication, Professor Fourrey has accepted our interpretation and agreed that the structure assigned to 8 in their paper should be revised.