C-glycosylation via radical cyclization: Synthetic application to a new C-glycoside

Tetrahedron Letters

Volumn 41, Issue 2, 2000, Pages 225-227

  Kim, Guncheol ^a   Kim, Hee Seok ^a  

^a Chungnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; HYDROXYL GROUP;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; GLYCOSYLATION; NONHUMAN; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0342393054     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02011-0     Document Type: Article

References (10)

1. Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20.
2. (b) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, 1995.
3. Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531.
4. (b) De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Winkler, T. Synlett 1994, 330-332.
5. (c) Kim, G.; Kang, S.; Kim, S. N. Tetrahedron Lett. 1993, 37, 7627-7628.
6. (d) Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7055.
7. The products are mixtures of E/Z isomers in a ca. 1:1 to 4:3 ratio. Following reactions were carried out with the mixtures.
8. 25=5.48 (c=0.006, MeOH).
9. Every protection condition of the hydroxyl group of 4 provided acetal intermediates. It is assumed that hemiacetal formation is dominated in the presence of base due to proximity between hydroxyl and aldehyde groups, although the groups exist separated in neutral condition.
10. -1, C=O) as described in the reference.