Oxidative macrocyclizations for the vancomycin antibiotics. Unexpected transannular effects in the thallium(III)-mediated M(2-4) macrocyclic ring closure

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3189-3192

  Evans, David A ^a   Dinsmore, Christopher J ^a   Ratz, Andrew M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

VANCOMYCIN DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0030942291     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00566-2     Document Type: Article

References (26)

1. (a) NIH Postdoctoral Fellow;
2. (b) DOD and Division of Organic Chemistry (ACS) predoctoral fellow.
3. (a) Atkinson, B. A. in Antibiotics in Laboratory Medicine; Lorian, V., Ed.; Williams and Wilkins: Baltimore, 1986, 995-1162.
4. (b) Glycopeptide Antibiotics; Nagarajan, R., Ed.; Marcel Dekker: New York, 1994.
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12. The seven amino acid residues are numbered consecutively, starting from the amino terminus. The M(X-Y) nomenclature refers to the macrocycle containing an oxidative crosslink between aryl groups of residues X and Y. Bicyclic moieties will be identified as M(X-Y)(Y-Z).
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14. (a) Evans, D. A.; Dinsmore, C. J.; Evrard, D. A.; DeVries, K. M. J. Am. Chem. Soc. 1993, 115, 6426-6427.
15. (b) Evans, D. A.; Dinsmore, C. J. Tetrahedron Lett. 1993, 34, 6029-6032.
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17. (a) Evans, D. A.; Dinsmore, C. J.; Ratz, A. M.; Evrard, D. A.; Barrow, J. C. J. Am. Chem. Soc. 1997, 119, in press.
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19. 4, morpholine, THF, 0 °C, 81%.
20. 4, morpholine, THF, 0 °C, 92%.
21. We speculate that this unstable intermediate is a spirocyclic oxazoline derived from intramolecular oxidative attack of the ring-3 amide oxygen onto ring-4. The use of isopropanol as solvent resulted in the same intermediate, as judged by tic on silica gel.
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26. 5; 3Å sieves]. Deuterated solvent was employed to assay for epimerization (d-incorporation) at the arylglycine-4 α-position via quinone methide formation; none was observed.