Trifluoroacetic acid-mediated facile transformation of 2-C-hydroxymethyl-d-glycals to chiral pyrano[2,3-b]benzopyrans

Carbohydrate Research

Volumn 344, Issue 4, 2009, Pages 521-525

  Santhi, Meenakshisundaram ^a   Balasubramanian, Kalpattu K ^a   Bhagavathy, Shanmugasundaram ^a  

^a Shasun Research Center   (India)

Author keywords

2 C Hydroxymethyl d glycal; Ferrier rearrangement; Intramolecular cyclization; Pyranobenzopyrans; Trifluoroacetic acid

Indexed keywords

2-C-HYDROXYMETHYL-D-GLYCAL; FERRIER REARRANGEMENT; INTRAMOLECULAR CYCLIZATION; PYRANOBENZOPYRANS; TRIFLUOROACETIC ACID;

CYCLIZATION; METHANOL; PHENOLS;

ACIDS;

2,3,5,12A TETRAHYDRO 2 BENZYLOXYMETHYL 3 BENZYLOXY [2,3 B]NAPHTHO[1,2 E]PYRAN; 2,3,5,12A TETRAHYDRO 2 METHOXYMETHYL 3 METHOXY [2,3 B]NAPHTHO[1,2 E]PYRAN; 3,10A DIHYDRO 2 BENZYLOXYMETHYL 3 BENZYLOXY 7 METHOXY 2H,5H PYRANO[2,3 B][1]BENZOPYRAN; 3,10A DIHYDRO 2 BENZYLOXYMETHYL 3 BENZYLOXY 7 METHYL 2H,5H PYRANO[2,3 B][1]BENZOPYRAN; 3,10A DIHYDRO 2 METHOXYMETHYL 3 METHOXY 7 METHY1 2H,5H PYRANO[2,3 B][1]BENZOPYRAN; BENZOPYRAN DERIVATIVE; CARBOHYDRATE DERIVATIVE; PHENOL; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ENVIRONMENTAL TEMPERATURE; PRIORITY JOURNAL; SYNTHESIS;

BENZOPYRANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; STEREOISOMERISM; TEMPERATURE; TRIFLUOROACETIC ACID;

EID: 61549110953     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2008.12.020     Document Type: Article

References (25)

1. Schweizer E.E., and Nyez-Meeder O. In: Ellis G.P. (Ed). The Chemistry of Heterocyclic Compounds Vol. 31 (1977), Wiley-Interscience, New York 11-139
2. Bowers W.S., Ohta T., Cleere J.S., and Marsella P.A. Science 193 (1976) 542-547
3. Yan M.C., Jang Y.J., and Yao C.F. Tetrahedron Lett. 42 (2001) 2717-2721
4. Nyerges M., Viranyi A., Marth G., Dancso A., Blasko G., and Toke L. Synlett (2004) 2761-2765
5. Bachman B., and Levine H.A. J. Am. Chem. Soc. 70 (1948) 599-601
6. Dauzonne D., and Rene R. Synthesis (1984) 348-349
7. Bandyopadhyay C., and Sur K.R. Indian J. Chem. 39B (2000) 137-140
8. Sosnovskikh V.Y., Korotaev V.Y., Chizhov D.L., Kutyashev I.B., Yachevskii D.S., Kazheva O.N., Dyachenko O.A., and Charushin V.N. J. Org. Chem. 71 (2006) 4538-4543
9. Booma C., and Balasubramanian K.K. Tetrahedron Lett. 34 (1993) 6757-6760
10. Yadav J.S., Reddy B.V.S., Aruna M., Venugopal C., Ramalingam T., Kumar S.K., and Kunwar A.C. J. Chem. Soc., Perkin Trans. 1 (2002) 165-171
11. Ghosh R., Chakraborty A., Maiti D.K., and Puranik V.G. Tetrahedron Lett. 46 (2005) 8047-8051
12. Ghosh R., Chakraborty A., Maiti D.K., and Puranik V.G. Org. Lett. 8 (2006) 1061-1064
13. Ferrier R.J., and Zubkov O.A. Org. React. 62 (2003) 571-625
14. Ferrier R.J. Top. Curr. Chem. 215 (2001) 153-175
15. Lin H.-C., Du W.-P., Chang C.C., and Lin C.H. Tetrahedron Lett. 46 (2005) 5071-5076
16. Toshima K., Matsuo G., Ishizuka T., Ushiki Y., Nakata M., and Matsumura S. J. Org. Chem. 63 (1998) 2307-2313
17. Li K., Foresee L.N., and Tunge J.A. J. Org. Chem. 70 (2005) 2881-2883
18. Svanholm U., and Parker V.D. J. Chem. Soc., Chem. Commun. (1972) 645-646
19. Svanholm U., and Parker V.D. J. Chem. Soc., Perkin Trans. 2 (1974) 169-173
20. Harwood L.M. J. Chem. Soc., Chem. Commun. (1982) 1120-1122
21. Mukaiyama T., Jona H., and Takeuchi K. Chem. Lett. (2000) 696-697
22. Fraser-Reid B., Walker D.L., Tam S.Y.-K., and Holder N.L. Can. J. Chem. 51 (1973) 3950-3954
23. Blackburne I.D., Fredericks P.M., and Guthrie R.D. Aust. J .Chem. 29 (1976) 381-391
24. Ramesh N.G., and Balasubramanian K.K. Tetrahedron Lett. 32 (1991) 3875-3878
25. Booma C., and Balasubramanian K.K. J. Chem. Soc., Chem. Commun. 18 (1993) 1394-1395