Template-directed intramolecular C-glycosidation. Synthesis of the central tetrahydrofuran fragment of the elfamycin antibiotic aurodox

Synlett

Volumn , Issue 11, 1998, Pages 1264-1266

  Craig, Donald ^a   Payne, Andrew H ^a   Warner, Peter ^b  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009485301     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-3144     Document Type: Article

References (24)

1. (i) Craig, D.; Munasinghe, V. R. N. Tetrahedron Lett. 1992, 33, 663-666;
2. (ii) Craig, D.; Pennington, M. W.; Warner, P. Tetrahedron Lett. 1993, 34, 8539-8542;
3. (iii) Craig, D.; Pennington, M. W.; Warner, P. Tetrahedron Lett. 1995, 36, 5815-5818.
4. Craig, D.; Payne, A. H.; Warner, P., submitted.
5. Dolle, R. E.; Nicolaou, K. C. J. Am. Chem. Soc. 1985, 107, 1691-1694;
6. Dolle, R. E.; Nicolaou, K. C. J. Am. Chem. Soc. 1985, 107, 1695-1698.
7. Martin and co-workers have reported extensively on intramolecular C-arylation of glycosides using cation-mediated transformations. See: Martin, O. R.; Hendricks, C. A. V.; Deshpande, P. P.; Cutler, A. B.; Kane, S. A.; Rao, S. P. Carbohydr. Res. 1990, 196, 1-58 and references therein.
8. D-Lyxonolactone was protected as the benzylidene acetal, triethylsilylated and reduced with DIBAL-H to give 5.
9. 13C nmr and IR spectra, and which showed low-resolution MS and either elemental combustion analysis or high-resolution MS characteristics in accord with the assigned structures.
10. 1(i) Separation of the isomers was carried out after desilylation; only the β-anomer was taken through the rest of the sequence.
11. The alcohol precursor of 11 was made by Cul-mediated addition of ethylmagnesium bromide to propargyl alcohol: Duboudin, J. G.; Jousseaume, B. J. Organometal. Chem. 1979, 168, 1-11.
12. We thank Mr Dick Sheppard and Mr Paul Hammerton of this department for these determinations.
13. We thank Professor David J. Williams and Dr Andrew J. P. White of this department for these determinations.
14. Clardy, J.; Evans, D. A.; Jones, T. K.; Kaldor, S. W.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031.
15. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3818.
16. Sullivan, G. R.; Dale, J. A.; Mosher, H. S. J. Org. Chem. 1973, 38, 2143-2147.
17. White, J. D.; Holoboski, M. A.; Green, N. J. Tetrahedron Lett. 1997, 38, 7333-7336.
18. Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 2065-2068.
19. 3, 75 MHz) 151.8, 138.5, 129.0, 128.6, 128.0, 126.5, 99.6, 91.7, 79.1, 76.6, 75.1, 70.8, 67.5, 56.1, 35.6, 29.4, 27.4, 17.7, 13.8, 11.5, 10.2, 6.8, 4.8.
20. E-3-Iodo-2-propen-1-ol was made by DIBAL-H reduction of methyl E-3-iodo-2-propenoate, which was prepared according to a literature procedure: Biougne, J.; Théron, F.; Normant, M. H. Comptes Rendus Acad. Sci. C 1971, 272, 858-861.
21. Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748-2749.
22. Yield based on recovered stannane (30% recovery).
23. +, 473.2723).
24. ZENECA in the U.K. is part of ZENECA Limited.