One-pot SmI2-promoted transformation of carbohydrate derivatives into cyclopentanols

Tetrahedron Letters

Volumn 37, Issue 32, 1996, Pages 5817-5820

  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

CYCLOALKANOL DERIVATIVE; CYCLOPENTANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030570848     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01234-8     Document Type: Article

References (13)

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3. 2. Enholm, E.J.; Trivellas, A. J. Am. Chem. Soc. 1989, 111, 6463. Enholm, E.J.; Satici, H.; Trivellas, A. J. Org. Chem. 1989, 54, 5891.
4. 3. Grové, J.J.C.; Holzapfel, C.W.; Williams, D.B.G. Tetrahedron letters 1996, 37, 1305.
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7. 10 followed by iodonation (NaI, acetone, reflux), furnished the title compound in an overall yield of ca. 70%.
8. 2 in THF (10.5 ml of a 0.1M solution) and HMPA (1.0 ml) was heated to reflux. Iodoglycoside (5) (0.21 mmol) in THF (10.0 ml) was added to this solution in a dropwise fashion during 10 min. The mixture was allowed to stir at that temperature for 2 h, after which it was allowed to cool to ambient temperature, and was diluted with 1:1 hexane/EtOAc (10.0 ml). Extraction (3×10 ml of a 5% aqueous citric acid, vacuum concentration and flash chromatography (5:1 hexane/ EtOAc) provided the pure cyclopentanol (7).
9. 5: 300.1937.
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12. 9. Chénedé, A.; Pothier, P.; Sollogoub, M.; Fairbanks, A.J., Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1995, 1373.
13. 10. Bolitt, V., Mioskowski, C. J. Org. Chem. 1990, 55, 5812.