New approach to the stereoselective synthesis of the [4.5] spiroketal moiety of papulacandins

Tetrahedron

Volumn 55, Issue 52, 1999, Pages 15159-15166

  Carretero, Juan C ^a   De Diego, J Eugenio ^b   Hamdouchi, Chafiq ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b CSIC   (Spain)

Author keywords

D arabino 1,4 lactone; Papulacandin; Spiroketal; , unsaturated sulfones

Indexed keywords

ACETAL; FURAN DERIVATIVE; LACTONE DERIVATIVE; PAPULACANDIN DERIVATIVE; SULFONE;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033601394     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/s0040-4020(99)00990-4     Document Type: Article

References (26)

1. a) Traxler, P.; Gruner, J.; Auden, J. A. L. J. Antibiot. 1977, 30, 289;
2. b) Traxler, P.; Fritz, H.; Richter, W. J. Helv. Chim. Acta 1977, 60, 578;
3. c) Traxler, P.; Fritz, H.; Fuhrer, H.; Richter, W. J. J. Antibiot. 1980, 33, 967.
4. a) Pérez, P.; García-Acha, I.; Durán, A. J. Gen. Microbiol. 1983, 129, 245;
5. b) Varona, R.; Pérez, P.; Durán, A. FEMS Microbiol. Lett. 1983, 20, 243.
6. a) Pérez, P.; Varona, R.; García-Acha, I.; Durán, A. FEBS Lett. 1981, 129, 249;
7. b) Baguley, B. C.; Römmele, G.; Gruner, J.; Wehrli, W. Eur. J. Biochem. 1979, 97, 345;
8. c) Römmele, G.; Traxler, P.; Wehrli, W. J. Antibiot. 1983, 36, 1539.
9. Previous degradation study by Traxler and co-workers demonstrated that the region of the aromatic is an attractive site for modifications, Traxler, P.; Tosch, W.; Zak, O. J. Antibiot. 1987, 40, 1146.
10. Danishefsky, S.; Phillips, G.; Ciufolini, M.; Carbohydr. Res. 1987, 171, 317.
11. a) Friesen, R. W.; Sturino, C. F. J. Org. Chem. 1990, 55, 5808;
12. b) Dubois, E.; Beau, J.-M. Carbohydr. Res. 1992, 223, 157;
13. c) Dubois, E.; Beau, J.-M. Tetrahedron Lett. 1990, 31, 5165;
14. d) Rosenblum, S. B.; Bihovsky, R. J. Am. Chem. Soc. 1990, 112, 2746.
15. a) Czernecki, S.; Perlat, M.-C. J. Org. Chem. 1991, 56, 6289;
16. b) Schmidt, R. R.; Frick, W. Tetrahedron 1988, 44, 7163;
17. c) Barrett, A. G. M.; Peña, M.; Willardsen, J. A. J. Chem. Soc., Chem. Commun. 1995, 11, 1147;
18. d) Barrett, A. G. M.; Peña, M.; Willardsen, J. A. J. Org. Chem. 1996, 61, 1082.
19. Carretero, J. C.; Rojo, J.; Díaz, N.; Hamdouchi, C.; Poveda, A. Tetrahedron 1995, 51, 8507.
20. Jain, S.; Shukla, K.; Mukhopadhyay, A.; Suryawanshi, S. N.; Bhakuni, D. S. Synth. Commun. 1990, 20, 1315.
21. Humphlett, W. J. Carbohydr. Res. 1967, 4, 157.
22. 2, benzaldehyde/camforsulfonic, and benzaldehyde dimethyl acetal/p-toluenesulfonic acid).
23. Probably due to the deactivation induced by the contiguous carbonyl group, the reactivity of the hydroxyl group at C-3 proved to be rather low. We recovered the starting material in the attempts to prepare the TBDMS (TBDMSCl/imidazole/DMAP or TBDMSOTf/2,6-lutidine), TES (TESCl/imidazole/DMPA) or MOM derivatives (MOMCl/di-iso-propyl ethyl amine).
24. In contrast the reaction of 1 with protected D-ribono-1,4-lactones gave a complex mixture of products, in which the corresponding spiroketals were not detected (see scheme below). Taking into account that the spiroketal formation by intramolecular addition of the alkoxide to the vinylsulfone moiety is a thermodynamically controlled process (ref. 8), the absence of the spiroketals from D-ribose derivatives could be explained by the presence of a strong 1,3-diaxial interaction between the oxygenated substituents at C-5/C-9 (see scheme below).
25. δ4 is much lower (about 0.9 ppm less) in related spiroketals of opposite configuration at C-4 (ref. 8).
26. 3 in methanol at rt).