A stereoselective carbohydrate route to optically activefuro[2,3-b]benzofuran ring system

Arkivoc

Volumn 2003, Issue 3, 2003, Pages 140-145

  Lakshmi, Rajamma ^a   Balasubramanian, Kalpattu K ^a  

^a Shasun Chemicals and Drugs Ltd   (India)

Author keywords

Aflatoxin; Claisen rearrangement; Ferrier rearrangement; Furo 2,3 b benzofuran; Stereoselective synthesis; Tri O acetyl D glucal

Indexed keywords

5 METHYL 2 ACETOXYMETHYL 3 ACETOXY 2,3,3A,8A TETRAHYDROFURO[2,3 B]BENZOFURAN; AFLATOXIN; FURO[2,3 B]FURAN DERIVATIVE; GLUCOSE; GLYCAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; HYDROLYSIS; ISOMER; OPTICAL ROTATION; OZONOLYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 3042703974     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (16)

1. (a) Giese, B.; Zeitz, G. H. Preparative Carbohydrate Chemistry; Hanessian, S.; Ed.; Marcel Dekker Inc.; New York, 1997, pp 507.
2. (b) Bols, M. Carbohydrate Building Blocks, John-Wiley & Sons: Toronto, 1996.
3. (c) Collins, P. M.; Ferrier, R. J.; Monosaccharides: Their Chemistry and Their Role in Natural Products, John Wiley & Sons, 1995.
4. (a) Buchi, G.; Foulkes, D. M.; Kurono, M.; Mitchell, F. G. J. Am. Chem. Soc. 1966, 89, 4534-4536.
5. (b) For a review see: Schuda, P. F. Topics in current chemistry, 1980, 91, 75-111.
6. (c) Castellino, A. J.; Rapoport, H. J. Org. Chem. 1986, 51, 1006-1011.
7. (d) Horne, S.; Weeratunga, G.; Rodrigo, R. J. Chem Soc.Chem Commun. 1990, 39-41.
8. (e) Gorst-Allman, P. C.; Steyn, P. S. J. Chem. Soc. Perkin Trans 1. 1987, 163-168.
9. (f) Weeratunga, G.; Horne, S.; Rodrigo, R. J. Chem Soc.Chem Commun. 1988, 721-722.
10. (g) Kraus, G. A.; Johnston, E. B.; Applegate, M. J. J. Org. Chem. 1991, 56, 5688-5691.
11. (h) Kraus G. A.; Wang, X. Tetrahedron Lett. 1999, 40, 8513-8514.
12. (a) Civitello, E. R..; Rapoport, H. J. Org. Chem. 1994, 59, 3775-82.
13. (b) Bando, T.; Shishido, K. Syn. Lett. 1997, 6, 665-666.
14. (c) Trost, B. M.; Toste, F. D. J.Am.Chem.Soc. 1999, 121, 3543-3544
15. Ramesh, N. G.; Pramanik, A.; Chandrasekhar, J.; Balasubramanian, K. K. J. Chem. Soc., Perkin Trans. II 1994, 1399-1401.
16. D'Souza, Francis; Cheshev, Pavel E.; Ayers, Joseph D.; Lowary, Todd L J.Org.Chem. 1998, 63, 9037-9044