A novel route to functionalized linearly benzannulated medium ring carbocyclics through regioselective aryl radical cyclization

Journal of the Indian Institute of Science

Volumn 81, Issue 3, 2001, Pages 239-264

  Ghosh, Keya ^a,c   Ghatak, Usha Ranjan ^a,b  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

^b INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^c ASUTOSH COLLEGE   (India)

Author keywords

Carbon carbon bond formation; Seven , eight , nine membered rings; Tertiary alcohol; Tributyltin hydride

Indexed keywords

CHEMICAL BONDS; DEHYDRATION; ESTERS; FREE RADICAL REACTIONS; OXIDATION;

RADICAL CYCLIZATION;

AROMATIC COMPOUNDS;

EID: 0035353827     PISSN: 09704140     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (48)

1. GIESE, B. Radicals in organic synthesis: Formation of carbon-carbon bonds, Pergamon Press, 1986.
2. JASPERSE, C. P., CURRAN, D. P. AND FEVIG, T. L. Radical reactions in natural product synthesis, Chem. Rev., 1991, 91, 1237-1286.
3. MOTHERWELL, M. B. AND CRICK, D. Free radical chain reactions in organic synthesis, Academic Press, 1991.
4. GIESE, B. et al. Radical cyclization, Org. React., 1996, 48, 301-856.
5. CURRAN, D. P., PORTER, N. A. AND GIESE., B. Strereochemistry of radical reactions, VCH Weinheim, 1996.
6. PATTENDEN, G. AND SANDEEP, H. Content. Org. Synth., 1997, 4, 196-215.
7. CLARK, A. J., JONES, K., McCARTHY, C. AND STOREY, J. M. D. Aryl radical cyclisations: quinoline, isoquinoline, and 1-benzazepin-2-one rings via 6- and 7-exo cyclisations, Tetrahedron Lett., 1991, 32, 2829-2832.
8. BOOTH, S. F., JENKINS, P. R. AND SWAIN, C. J. The synthesis of bicyclic and tricyclic ring systems by radical cyclisation reactions of oxime ethers, J. Chem. Soc., Chem. Commun., 1991, 1248-1249.
9. BOGER, D. L. AND MATHVINK, R. J. Intramolecular and intramolecular alkene addition reactions, J. Org. Chem., 1992, 57, 1429-1443.
10. KIM, S. AND KEE, I. S. Further studies on radical cyclisation of N-aziridinyl imines. Carbonyl and alkenyl group vs N-aziridinyl imino group competition, Tetrahedron Lett., 1993, 34, 4213-4214.
11. MOODY, C. J. AND NORTON, C. L. Synthesis of 1,2-fused indoles by radical cyclisation, Tetrahedron Lett., 1995, 36, 9051-9052.
12. MIYABE, H., TORIEDA, M., KIGUCHI, T. AND NAITO, T. Total synthesis of (-)-balanol, Synlett, 1997, 580-582.
13. YUASA, Y., SATO, W. AND SHIBUYA, S. Diastereoselective synthesis of cyclic ethers by radical cyclisation at β-position of β-alkoxyacrylates, Synth. Commun., 1997, 27, 573-585.
14. EVANS, P. A. AND MANANGAN, T. Vinylogous sulfonates as radical acceptors for the stereoselective synthesis of cyclic ethers, Tetrahedron Lett., 1997, 38, 8165-8168.
15. SILVANA, M. L. AND PAQUETTE, L. A. Intramolecular cyclization of radicals generated from α-halomethyl sulfonamides, J. Org. Chem., 1999, 64, 9225-9229.
16. ABEYWICKREMA, A. N., BECKWITH, A. L. J. AND GERBA, S. J. Consecutive ring closure and neophyl rearrangement of some alkenylaryl radicals, J. Org. Chem., 1987, 52, 4072-4078.
17. ABEYWICKSEMA, A. N. AND BECKWITH, A. L. J. Rate constants for the cyclisation of some aryl radicals bearing unsaturated ortho-substituents, J. Chem., Soc., Chem. Commun., 1986, 464-465.
18. BECKWITH, A. L. J. Regio-selectivity and stereo-selectivity in radical reactions, Tetrahedron, 1981, 37, 3073-3100.
19. BECKWITH, A. L. J., EASTON, C. J. AND SERELIS, A. K. Some guidelines of radical reactions, J Chem. Soc., Chem. Commun., 1980, 482-483.
20. BECKWITH, A. L. J. AND GARA, W. B. Mechanism of cyclization of aryl radicals containing unsaturated ortho-substituents, J. Chem. Soc., Perkin Trans. 2, 1975, 795-802.
21. BANIK, B. Tributyltin hydride induced intramolecular aryl radical cyclizations: Synthesis of biologically interesting organic compounds, Curr. Org. Chem., 1999, 3, 469-496.
22. YET, L. Free radicals in the synthesis of medium-sized rings, Tetrahedron, 1999, 55, 9349-9403.
23. PAL, S., MUKHERJEE, M., PODDER, D., MUKHERJEE, A. K. AND GHATAK, U. R. A highly regioselective 6-endo-aryl radical cyclisation: Stereocontrolled synthesis of trans-octahydro anthracenes, J. Chem. Soc., Chem. Commun., 1991, 1591-1593.
24. PAL, S., MUKHOPADHYAYA, J. K. AND GHATAK, U. R. Regioselective aryl radical cyclisation 1. Stereocontrolled synthesis of linearly condensed hydroaromatic carbocyclic systems through 6 endo-ring closures, J. Org. Chem., 1994, 59, 2687-2694.
25. GHOSH, A. K., GHOSH, K., PAL, S. AND GHATAK, U. R. Highly regioselective 7-endo-aryl radical cyclisation: Synthesis of octahydro-2H-dibenzo[a,d]cycloheptanes, J. Chem. Soc., Chem. Commun., 1993, 809-811; Corrigendum, 1176.
26. GHOSH, A. K., MUKHOPADHYAYA, J. K. AND GHATAK, U. R. Regioselective aryl radical cyclization. Part 2. Synthesis of octahydro-1H-dibenzo[a,d]cycloheptanes through 7-endo ring closure, J. Chem. Soc., Perkin Trans. 1, 1997, 2747-2755.
27. MARCO-CONTELLES, J. AND dEOPAZO, E. Synthesis of chiral, densely functionalized medium-sized rings from carbohydrate precursors via regioselective exo/endo primary alkyl radical cyclization, Tetrahedron Lett., 2000, 41, 5341-5345, and references cited therein.
28. GHOSH, K., GHOSH, A. K. AND GHATAK, U. R. Highly regioselective 8-endo-aryl radical cyclization: new synthetic route to decahydrodibenzo-[a,d]- and -[a,e]-cyclooctanols, J. Chem. Soc., Chem. Commun., 1994, 629-630.
29. GHOSH, K. AND GHATAK, U. R. Regioselective 9-endo aryl radical cyclisation: A novel synthetic route to decahydro-5H-dibenzo[a,d]cyclononenols, Tetrahedron Lett., 1995, 36, 4897-4900.
30. PETASIS, N. A. AND PATANE, M. A. The synthesis of carbocyclic eight-membered rings, Tetrahedron, 1992, 46, 5757-5821.
31. ROXBURGH, C. J. Synthesis of medium-sized rings by ring expansion reactions, Tetrahedron, 1993, 49, 10749-10784.
32. MOLANDER, G. A. Diverse methods for medium ring synthesis, Acc. Chem. Res., 1998, 31, 603-609.
33. MEHTA, G. AND SINGH, V. Progress in the construction of cyclooctanoid systems. New approaches and applications to natural product synthesis, Chem. Rev., 1999, 99, 881-930.
34. PIERS, E., WALKERS, S. D. AND ARMBRUST, R. A new cycloheptenone annulation method: Use of the bifunctional reagent (Z)-5-iodo-1-tributylstannylpent-1-ene in organic synthesis, J. Chem. Soc., Perkin Trans. 1, 2000, 635-637.
35. BECKWITH, A. L. J. AND SCHESSER, C. H. Regio- and stereo-selectivity of alkenyl radical ring closure: A theoretical study, Tetrahedron, 1985, 41, 3925-3941.
36. FINCH, H., PEGG, N. A. AND EVANS, B. The synthesis of a conformationally restrained, combined thromboxane antagonist/synthase inhibitor using an intramolecular 'Stille'- or 'Grigg'-palladium catalysed cyclisation strategy, Tetrahedron Lett., 1993, 34, 8353-8356.
37. GIBSON, S. E., GUILLO, N. AND TOZER, M. Application of 7-endo, 8-endo, 9-endo radical cyclization to the synthesis of conformationally constrained amino acids and comparison with the corresponding Heck reactions, J. Chem. Soc., Chem. Commun., 1997, 637-638.
38. HIRST, G.C., HOWARD, P. N. AND OVERMAN, L.E. Stereocontrolled construction of carbocyclic rings sequential cationic cyclization-pinacol rearrangement, J. Am. Chem. Soc., 1989. 11, 1514-1515, and references cited therein.
39. FADEL, A. AND SALAUN, J. Anhydrous ferric chloride adsorbed on silica gel induced ring enlargement of tertiary cyclobutanols, Tetrahedron, 1985, 41, 413-420.
40. BLOMBERG, C. AND HARTOG, F. A. The Barbier reactions-a one-step alternative for synthesis via organomagnesium compounds, Synthesis, 1977, 18-30.
41. ANDO, K. et al. Stereoselectivities of nucleophilic additions to cycloheptanones. Experimental and theoretical studies and general purpose force field for the production of nucleophilic addition Stereoselectivities, J. Org. Chem., 1998, 63, 3196-3203.
42. GHATAK, U. R., CHAKRAVARTY, J. AND BANERJEE, A. K. Synthetic studies directed to gibberellens and related compounds, Tetrahedron, 1968, 24, 1577-1593.
43. CHANG, F. C. AND WOOD, N. F. Reactions of potassium tert-butoxide in dimethyl sulfoxide. III. Hydrolysis of hindered carboxylic ester, Tetrahedron Lett., 1964, 2969-2973.
44. GHOSH, K. AND PRAMANIK, A. (IRS, 4aSR, 12aSR)-1-Methyl-1,2,3,4a,5,6-7,12,12a-decahydrodibenzo-[a,d]cyclooctene-1,4a-car bolactone, Acta Cryst. C, 1996, 52, 1029-1030.
45. SHAIK, S. S. AND CANADELL, E. Regioselectivity of radical attacks on substituted olefins. Application of the SCD model, J. Am. Chem. Soc., 1990, 112, 1446-1452.
46. MUKHOPADHYAYA, J. K., PAL, S. AND GHATAK, U. R. A novel route to functionalized linearly benzannulated cycloheptene and cyclooctene derivatives through regioselective aryl radical cyclization. Indian J. Chem. B, 1999, 38, 264-268.
47. CHATTOPADHYAYA, P., MUKHERJEE, M. AND GHOSH, S. A simple construction of chiral fused benzocine ring ethers from D(+)-glucose by 8-endo-aryl radical cyclization, J. Chem. Soc., Chem. Commun., 1997, 2139-2140.
48. BANERJEE, A. Unpublished results.