A three-step and enantioselective synthesis of (-)-(S)- or (+)-(R)-2- (furan-3-yl)-3,6-dihydro-2H-pyrans

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1593-1596

  De Rosa, Margherita ^a   Solladié Cavallo, Arlette ^b   Scettri, Arrigo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Asymmetric allylation; Furyl dihydropyranes; Ring closing metathesis

Indexed keywords

CACOSPONGIONOLIDE B; FURAN DERIVATIVE; MANOALIDE; PYRAN DERIVATIVE; PYRANOFURANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DRUG STRUCTURE; ENANTIOMER; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 17344376516     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02337-0     Document Type: Article

References (16)

1. De Rosa, S.; Crispino, A.; De Giulio, A.; Iodice, C.; Pronzato, R.; Zavodnik, N. J. Nat. Prod. 1995, 58, 1776.
2. De Silva, E. D.; Scheuer, P. J. Tetrahedron Lett. 1980, 21, 1611.
3. Potts, B. C.; Faulkner, M. D. J.; De Carvalho, M. S.; Jacobs, R. S. J. Am. Chem. Soc. 1992, 114, 5093.
4. De Rosa, M.; Giordano, S.; Scettri, A.; Sodano, G.; Soriente, A.; Pastor, P. G.; Alcaraz, M. J.; Payá, M. J. Med. Chem. 1998, 41, 3232.
5. (a) De Rosa, M.; Dell'Aglio, R.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 1999, 10, 3659.
6. (b) Soriente, A.; De Rosa, M.; Scettri, A.; Sodano G. Tetrahedron Lett. 1996, 37, 8007.
7. (c) Soriente, A.; De Rosa, M.; Dovinola, P.; Soddano, G.; Scettri, A. Tetrahedron Asymmetry 1998, 9, 2197.
8. Racherla, U. S.; Liao, Y.; Brown, H. C. J. Org. Chem. 1992, 57, 6614.
9. (a) Grubbs, H. R.; Chang, S. Tetrahedron 1998, 54, 4413.
10. (b) Armstrong, K. S. J. Chem. Soc., Perkin Trans. 1 1998, 371.
11. 2: C, 69.54; H, 7.30. Found C, 69.47; H, 7.39.
12. 3. The specific rotations are, by far, less precise either being measured from small quantities of compounds (weight <50 mg) or because of non-linear effects.
13. Girard, C.; Kagan, H. Angew. Chem., Int. Ed. 1998, 37, 2922.
14. 3).
15. 3).
16. 2: C, 73.15; H, 7.37. Found C, 73.06; H, 7.43.