Densely functionalized chiral pyrroles from endocyclic, exocyclic, and acyclic vinyl sulfone-modified carbohydrates

Journal of Organic Chemistry

Volumn 74, Issue 2, 2009, Pages 669-674

  Bhattacharya, Rahul ^a   Atta, Ananta Kumar ^a   Dey, Debanjana ^a   Pathak, Tanmaya ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONALIZED; PYRANOSYL RINGS; PYRROLE DERIVATIVES; STARTING MATERIALS; VINYL SULFONES;

CARBOHYDRATES; FABRICS; NITROGEN COMPOUNDS;

POTASSIUM COMPOUNDS;

CARBOHYDRATE; DIETHYL 3,3' (2,2 DIMETHYL 1,3 DIOXOLANE 4,5 DIYL) BIS (1H PYRROLE 2 CARBOXYLATE); ETHYL 3 (1,2 DIMETHOXYETHYL) 1H PYRROLE 2 CARBOXYLATE; ETHYL 3 (6 METHOXY 2,2 DIMETHYTETRAHYDROFURO[2,3 D][1,3]DIOXOL 5 YL) 1H PYRROLE 2 CARBOXYLATE; ETHYL 3 [ 2 (BENZYLOXY) 1 HYDROXYETHYL] 4 FORMYL 1H PYRROLE 2 CARBOXYLATE; ETHYL 3 FORMYL 4 (5 HYDROXY 2 PHENYL 1,3 DIOXAN 4 YL) 1H PYRROLE 2 CARBOXYLATE; ETHYL 4 (6 METHOXY 2,2 DIMETHYLTETRAHYDROFURO[2,3 D][1,3]DIOXOL 5 YL) 1H PYRROLE 2 CARBOXYLATE; ETHYL 4 [ 1,4 DIOXASPIRO[4.5]DEC 2 YL(HYDROXY)METHYL ] 3 FORMYL 1H PYRROLE 2 CARBOXYLATE; ETHYL 4 [ 2 (BENZYLOXY) 1 HYDROXYETHYL] 3 FORMYL 1H PYRROLE 2 CARBOXYLATE; ETHYL 4 FORMYL 3 (5 HYDROXY 2 PHENYL 1,3 DIOXAN 4 YL) 1H PYRROLE 2 CARBOXYLATE; ETHYL 6 METHOXY 2 PHENYL 4A,6,8,9B TETRAHYDRO 4H [1,3]DIOXINO[4',:5,6]PYRANO[3,4 C]PYRROLE 7 CARBOXYLATE; ETHYL 6 METHOXY 2 PHENYL 4A,6,8,9B TETRAHYDRO 4H [1,3]DIOXINO[4',:5,6]PYRANO[3,4 C]PYRROLE 9 CARBOXYLATE; ETHYL 7 (BENZYLOXY) 6 METHOXY 4 (TRIPHENYLMETHYLOXYMETHYL) 2,4,6,7 TETRAHYDROPYRANO[3,4 C]PYRROLE 1 CARBOXYLATE; ETHYL 7 (BENZYLOXY) 6 METHOXY 4 METHYL 2,4,6,7 TETRAHYDROPYRANO[3,4 C]PYRROLE 1 CARBOXYLATE; ETHYL 7 BENZYLOXY 6 (BENZYLOXYMETHYL) 4 METHOXY 2,4,6,7 TETRAHYDROPYRANO[3,4 C]PYRROLE 3 CARBOXYLATE; PYRROLE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; DIVINYL SULFONE; SULFONE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; SYNTHESIS; CHEMISTRY; STEREOISOMERISM;

CARBOHYDRATES; PYRROLES; STEREOISOMERISM; SULFONES;

EID: 60849109225     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801948m     Document Type: Article

References (22)

1. th ed.; Blackwell Publishing: Cambridge, MA, 2003; pp 237-272.
2. Chiba, S.; Wang, Y.-F.; Lapointe, G.; Narasaka, K. Org. Lett. 2008, 10, 313, and references cited therein.
3. For reviews on pyrroles, see: (a) Ono, N. Heterocycles 2008, 75, 243.
4. (b) Fan, H.; Peng, J.; Hamann, M. T.; Hu, J.-F. Chem. Rev. 2008, 108, 264.
5. (c) Schmuck, C.; Rupprecht, D. Synthesis 2007, 20, 3095.
6. Halazy, S.; Magnus, P. Tetrahedron Lett. 1984, 25, 1421.
7. (a) Finikova, O. S.; Cheprakov, A. V.; Vinogradov, S. A. J. Org. Chem. 2005, 70, 9562.
8. (b) Finikova, O. S.; Cheprakov, A. V.; Beletskaya, I. P.; Carroll, P. J.; Vinogradov, S. A. J. Org. Chem. 2004, 69, 522.
9. (c) Hwang, S. H.; Kurth, M. J. J. Org. Chem. 2002, 67, 6564.
10. (d) Abel, Y.; Haake, E.; Haake, G.; Schmidt, W.; Struve, D.; Walter, A.; Montforts, F. P. Helv. Chim. Acta 1998, 81, 1978.
11. (e) Sumi, K.; Di Fabio, R.; Hanessian, S. Tetrahedron Lett. 1992, 33, 749.
12. (f) Padwa, A.; Norman, B. H. J. Org. Chem. 1990, 55, 4801.
13. (a) Uno, H.; Sahara, Y.; Takiue, T. Tetrahedron Lett. 2007, 48, 7825.
14. (b) Okujima, T.; Komobuchi, N.; Uno, H.; Ono, N. Heterocycles 2006, 67, 255.
15. (c) Cheng, W.-C.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 2001, 66, 5528.
16. 30c
17. There are scant reports on the synthesis of sugar linked pyrroles. In these cases the aldehydo group of sugar molecule was directly reacted with pyrrole, see: Yadav, J. S.; Reddy, B. V. Subba; Satheesh, G. Tetrahedron Lett. 204, 45, 3673. Casiraghi, G.; Cornia, M.; Zanardi, F.; Rassu, G.; Ragg, E.; Bortolini, R. J. Org. Chem. 1994, 59, 1801.
18. Pathak, T. Tetrahedron. 2008, 64, 3605.
19. Das, I.; Pal, T. K.; Suresh, C. G.; Pathak, T. J. Org. Chem. 2007, 72, 5523.
20. Saeki, H.; Iwashige, T.; Ohki, E. Chem. Pharm. Bull. 1968, 16, 1040.
21. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C. J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598.
22. Le Merrer, Y.; Dureault, A.; Greck, C.; Micas, L. D.; Gravier, C.; Depezay, J. C. Heterocycles 1987, 25, 541.