Toward a total synthesis of an aglycone of spiramycin; a chiron approach to the C-1/C-4 and the C-13/C-15 fragments

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6607-6610

  Breullles, P ^a   Oddon, G ^a   Uguen, D ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DIOXANE DERIVATIVE; SPIRAMYCIN;

ARTICLE; DRUG SYNTHESIS;

CHIRON;

EID: 0030805968     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01523-2     Document Type: Article

References (14)

1. Oddon, G.; Uguen, D. Tetrahedron Lett. 1997, 38, 4411-4414.
2. Keck, G. E.; Palani, A.; McHardy, S. F. J. Org. Chem. 1994, 59, 3113-3122.
3. a) Hanessian, S.; Ugolini, A.; Therien, M. J. Org. Chem. 1983, 48, 4427-4430;
4. b) Saito, S.; Ishikawa, T.; Kuroda, A.; Koga, K.; Moriwake, T. Tetrahedron 1992, 48, 4067-4086. (R)-malic could be conveniently prepared from (R,R)-tartaric acid on a 100 g-scale by using a published procedure (Gao, Y; Zepp, C. M. Tetrahedron Lett. 1991, 32, 3155-3158).
5. b) Saito, S.; Ishikawa, T.; Kuroda, A.; Koga, K.; Moriwake, T. Tetrahedron 1992, 48, 4067-4086. (R)-malic could be conveniently prepared from (R,R)-tartaric acid on a 100 g-scale by using a published procedure (Gao, Y; Zepp, C. M. Tetrahedron Lett. 1991, 32, 3155-3158).
6. a) Herradon, B.; Cueto, S.; Morcuende, A.; Valverde, S. Tetrahedron: Asymmetry 1993, 4, 845-864;
7. b) Tsuri, T.; Kamata, S. Tetrahedron Lett. 1985, 26, 5195-5198.
8. 1H NMR, by integration of singlets at 5.5, 5.76 and 5.9 ppm, respectively, corresponding to the acetalic proton of each isomeric acetal.
9. Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358.
10. 2). Attempted similar acetalisation of benzaldehyde proved not so satisfactory: the reaction did not proceed before the temperature rose -20 °C and, in these conditions, a mixture of dioxane and dioxolane derivatives was formed.
11. Compare with: Oikawa, H.; Matsuda, I.; Ichihara, A.; Kohmoto, K. Tetrahedron Lett. 1994, 35, 1223-1226. The TIPS group of R-5c prevents probably the complexation of DIBA-H by the two vicinal oxygen atoms, what explains the observed high regioselectivity of that reductive ring-opening step.
12. D values have been measured at 21 °C.
13. Gerlach, H.; Oertle, K.; Thalmann, A. Helv. Chim. Acta 1976, 59, 755-760.
14. The results presented herein are taken in parts from the thesis dissertation of G. Oddon (Université Louis Pasteur, Strasbourg, 1996).