Studies on thiopeptide antibiotics: Aynthesis of an oxazole-thiazole-pyridine fragment related to promothiocin A

Synlett

Volumn , Issue 4, 1998, Pages 361-362

  Moody, Christopher J ^a   Bagley, Mark C ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001846793     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1670     Document Type: Article

References (25)

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15. The rhodium(II) catalysed N-H insertion and subsequent cyclodehydration reactions were carried out as described in reference 10.
16. 3); the optical purity was confirmed as >99% by HPLC on a chiral stationary phase (Chiralpak AD, hexane : 2-propanol, 9 : 1, 1.0 ml/min) by comparison with the racemate.
17. Bram, G.; Vilkas, M. Bull. Soc. Chim. Fr. 1964, 945;
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19. Baraldi, P. G.; Simoni, D.; Manfredini, S. Synthesis 1983, 902.
20. 2Me).
21. Prepared by addition of ethynylmagnesium bromide to benzyloxyacetaldehyde in THF (86%), followed by oxidation to the ketone with o-iodoxybenzoic acid (IBX) in DMSO (89%). For oxidations with IBX, see: Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
22. 2Me).
23. Bredenkamp, M. W.; Holzapfel, C. W.; Snyman, R. M.; vanZyl, W. J. Synth. Commun. 1992, 22, 3029;
24. Aguilar, E.; Meyers, A. I. Tetrahedron Lett. 1994, 35, 2473.
25. 2), 44.7 (CH), 28.3 (Me), 20.3 (Me), 14.3 (Me), and 11.1 (Me).