First synthesis of (±)-1α,2α,4β-trihydroxycyclohex-5-ene. Anchimeric assistance in conduritol syntheses

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4393-4396

  Haines, Alan H ^a   King, Amy S H ^a   Knight, Jonathan R ^a   Nguyen, Viet Anh ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE; 1ALPHA,2ALPHA,4BETA TRIHYDROXYCYCLOHEX 5 ENE; CONDURITOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

EID: 0032508069     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00745-X     Document Type: Article

References (29)

1. 1. Balci, M.; Sütbeyaz, Y.; Seçen, H. Tetrahedron, 1990, 46, 3715.
2. 2. Guo, Z.-X.; Haines, A. H.; Pyke, S. M.; Pyke, S. G.; Taylor, R. J. K. Carbohydr. Res., 1994, 264, 147.
3. 3. Gal, A. E.; Voorstaad, J. P. J. Labelled Compd. Radiopharm., 1987, 24, 397.
4. 4. Prévost, C. C. R. Hebd. Seances Acad, Sci., 1933, 196, 1129; Prévost, C. C. R. Hebd. Seances Acad. Sci., 1933, 197, 1661.
5. 4. Prévost, C. C. R. Hebd. Seances Acad, Sci., 1933, 196, 1129; Prévost, C. C. R. Hebd. Seances Acad. Sci., 1933, 197, 1661.
6. 5. Gunstone, F. D. Adv. Org. Chem., 1960, 1, 103.
7. 6. Woodward, R. B.; Brutcher, Jr., F. B. J. Am. Chem. Soc., 1958, 80, 209; see also Woodward, R. B. U.S. Patent, 2, 687, 435 (1954); CA 1955, 49, 14809.
8. 6. Woodward, R. B.; Brutcher, Jr., F. B. J. Am. Chem. Soc., 1958, 80, 209; see also Woodward, R. B. U.S. Patent, 2, 687, 435 (1954); CA 1955, 49, 14809.
9. 6. Woodward, R. B.; Brutcher, Jr., F. B. J. Am. Chem. Soc., 1958, 80, 209; see also Woodward, R. B. U.S. Patent, 2, 687, 435 (1954); CA 1955, 49, 14809.
10. 7. All compounds mentioned in this paper are racemates, although the formulae and corresponding names refer to one enantiomer only. All new compounds gave satisfactory elemental analyses or high resolution mass spectral data.
11. 8. Seçen, H.; Salamci, E.; Sütbeyaz, Y.; Balci, M. Synlett, 1993, 609.
12. 9. Salamci, E.; Seçen, H.; Sütbeyaz, Y.; Balci, M. J. Org, Chem., 1997, 62, 2453.
13. 10. O'Brien, P; Poumellec, P. Tetrahedron Lett., 1996, 37, 8057.
14. 11 Motherwell, W. B.; Williams, A. S. Angew. Chem. Int. Ed. Engl., 1995, 34, 2031. We thank Professor W. B. Motherwell for providing unpublished data on this compound.
15. 12. Knight, J. R. Synthetic studies towards the conduritols, University of Bristol, U.K., 1996.
16. 3) 20.69, 20.71, 20.97, (3 x MeCO), 23.82 (CHI), 67.04, 73.27, 73.65, (3 x CHOAc), 126.64, 128.51 (2 x -CH=), 170.59, 170.71, 170.88 (3 x CO).
17. 3) 20.58, 20.65, 20.86 (3 x MeCO), 47.28 (CHBr), 67.78, 72.20, 72.26 (3 x CHOAc), 126.70, 128.43 (2 x -CH=), 169.88, 170.08, 170.19 (3 x CO).
18. 2), 66.01, 67.08, 67.30 (3 x CHOAc), 127.92, 130.29 (2 x -CH=), 170.54, 170.61, 170.75 (3 x CO).
19. 2), 65.35, 67.80, 68.50 (3 x CHOH), 130.27, 133.06 (2 x -CH=).
20. 13C NMR data on tetraacetates of the conduritols are contained in the following references: (a) conduritol-A, Sütbeyaz, Y; Seçen, H; Balci, M. J. Chem. Soc., Chem. Commun., 1988, 1330.
21. (b) conduritol-B, ref. 18.
22. (c) conduritol-C, Seçen, H; Maras, A; Sütbeyaz, Y.; Balci, M. Synth. Commun., 1992, 22, 2613.
23. (d) conduritol-D, ref. 12.
24. (e) conduritol-E, ref. 17(c).
25. (f) conduritol-F, ref. 18.
26. 18. Le Drian, C.; Vionnet, J.-P.; Vogel, P. Helv. Chim. Acta, 1990, 73, 161.
27. 19. Seçen, H.; Sütbeyaz, Y.; Balci, M. Tetrahedron Lett., 1990, 31, 1323.
28. 13C NMR spectra of the tetraacetate of conduritol-C.
29. 3OD) 59.56 (CHBr), 69.46, 71.00, 75.91 (3 x CHOH), 130.29, 131.21 (2 x -CH=).