Stereoselective SmI2-mediated conversion of carbohydrates into cyclopentanols

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1305-1308

  Grové, J J Cronjé ^a   Holzapfel, Cedric W ^a   Williams, D Bradley G ^a  

^a UNIVERSITY OF JOHANNESBURG   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030044238     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02380-1     Document Type: Article

References (19)

1. Verheyden, J.P.H.; Richardson, A.C.; Bhatt, R.S.; Grant, B.D.; Fitch, W.L.; Moffatt, J.G. Pure Appl. Chem. 1978, 50, 1363.
2. Ferrier, R.J.; Middleton, S. Chem. Rev. 1993, 93, 2779, and references therein cited.
3. Collins, P.W.; Djuric, S.W. Chem. Rev. 1993, 93, 1533.
4. Enholm, E.J.; Trivellas, A. J. Am. Chem. Soc. 1989, 111, 6463. Enholm, E.J.; Satici, H.; Travellas, A. J. Org. Chem. 1989, 54, 5891.
5. Enholm, E.J.; Trivellas, A. J. Am. Chem. Soc. 1989, 111, 6463. Enholm, E.J.; Satici, H.; Travellas, A. J. Org. Chem. 1989, 54, 5891.
6. Enholm, E.J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063. Molander, G.A.; Kenny, C. J. Org. Chem. 1988, 53, 2132.
7. Enholm, E.J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063. Molander, G.A.; Kenny, C. J. Org. Chem. 1988, 53, 2132.
8. Molander, G.A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236. Molander, G.A.; Kenny, C. J. Org. Chem. 1991, 56, 1439.
9. Molander, G.A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236. Molander, G.A.; Kenny, C. J. Org. Chem. 1991, 56, 1439.
10. 4 418.2144.
11. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990. Ferrier, R.J.; Prasit, P. J. Chem. Soc., Chem. Comm. 1981, 983.
12. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990. Ferrier, R.J.; Prasit, P. J. Chem. Soc., Chem. Comm. 1981, 983.
13. Williams, D.B.G. New Routes to Multicyclic Compounds, Rand Afrikaans University 1995.
14. 2 in THF (10.5 ml of a 0.1 M solution, 1.05 mmol) was added dropwise during 15 min. The reaction mixture was allowed to warm to 0°C during 30 min., at which time it was diluted with 1:1 hexane/EtOAc (30 ml) and washed with aqueous citric acid (20 ml of a 5% solution). The solvent was removed under reduced pressure, and the residue was chromatographed (4:1 hexane/EtOAc) on silica.
15. Pratt, D.V.; Hopkins, P.B. Tetrahedron Lett. 1987, 28, 3065. White, J.D.; Somers, T.C. J. Am. Chem. Soc. 1987, 109, 4424.
16. Pratt, D.V.; Hopkins, P.B. Tetrahedron Lett. 1987, 28, 3065. White, J.D.; Somers, T.C. J. Am. Chem. Soc. 1987, 109, 4424.
17. Hanessian, S.; Girard, C.; Chiara, J.L. Tetrahedron Lett. 1992, 33, 573.
18. Grové, J.J.C.; Holzapfel, C.W.; Williams, D.B.G. unpublished results.
19. Molander, G.A.; McKie, J.A. J. Org. Chem. 1995, 60, 872.