Regio- and stereochemical aspects in synthesis of 2-allyl derivatives of glycolic, mandelic and lactic acids and their iodocyclisations to 3-hydroxy-3,4-dihydrofuran-2(5H)-ones

Tetrahedron

Volumn 61, Issue 34, 2005, Pages 8231-8240

  Kaur, Pervinder ^a   Singh, Palwinder ^a   Kumar, Subodh ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

Diastereoselective; Furan 2 ones; Indium allylation; Iodocyclisations

Indexed keywords

ALLYL COMPOUND; FURAN DERIVATIVE; GLYCOLIC ACID DERIVATIVE; LACTIC ACID; MANDELIC ACID;

ALKYLATION; ARTICLE; CYCLIZATION; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 22544435507     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.06.045     Document Type: Article

References (40)

1. C.C. Shen, C.L. Ni, Y.L. Huang, R.L. Huang, and C.C. Chen J. Nat. Prod. 67 2004 1947 1949
2. A.E. Hadri, A. Abouabdellah, U. Thomet, R. Baur, R. Furtmuller, E. Sigel, W. Sieghart, and R.H. Dodd J. Med. Chem. 45 2002 2824 2831
3. T. Janecki, K. Blaszczyk, K. Studzian, M. Rozalski, U. Krajewska, and A. Janecka J. Med. Chem. 45 2002 1142 1145
4. S.P. Khanapure, D.S. Garvey, D.V. Young, Y.M. Ezawa, R.A. Earl, R.D. Gaston, X. Fang, M. Murty, A. Martino, M. Shumway, M. Trocha, P. Marek, S.W. Tam, D.R. Janero, and L.G. Letts J. Med. Chem. 46 2003 5484 5504
5. Y. Liu, T.A. Mansoor, J. Hong, C.O. Lee, C.J. Sim, K.S. Im, N.D. Kim, and J.H. Jung J. Nat. Prod. 66 2003 1451 1456
6. A.G.H. Wee, and Q. Yu J. Org. Chem. 66 2001 8935 8943
7. J.N.C. Franklin, and A. Butler J. Am. Chem. Soc. 126 2004 15060 15066
8. H.C. Brown, S.V. Kulkarni, and U.S. Rachelerla J. Org. Chem. 59 1994 365 369
9. G. Cardillio, and M. Orena Tetrahedron 46 1990 3321 3408
10. A.R. Chamberlin, M. Dezube, P. Dussault, and M. McMills J. Am. Chem. Soc. 105 1983 5819 5825
11. M. Curini, F. Epifano, M.C. Marcotullio, and F. Montanari Synlett 2004 368 370
12. M. Wang, L.X. Gao, W.P. Mai, A.X. Xia, F. Wang, and S.B. Zhang J. Org. Chem. 69 2004 2874 2876
13. J. Haas, S. Piguel, and T. Wirth Org. Lett. 4 2002 297 300
14. Z. Wang, X. Meng, and G.W. Kabalka Tetrahedron Lett. 32 1991 4619 4622
15. Z. Wang, X. Meng, and G.W. Kabalka Tetrahedron Lett. 32 1991 5677 5680
16. Z. Wang, G. Xu, D. Wang, M.E. Pierce, and P.N. Confalone Tetrahedron Lett. 41 2000 4523 4526
17. M. Wada, M. Honna, Y. Kuramoto, and N. Miyoshi Bull. Chem. Soc. Jpn. 70 1997 2265 2267
18. M. Wada, T. Fukuma, M. Morioka, T. Takahashi, and N. Miyoshi Tetrahedron Lett. 38 1997 8045 8048
19. For reviews see: (a) P. Cintas Synlett 1995 1087 1096
20. C.J. Li Tetrahedron 52 1996 5643 5668
21. C.J. Li, and T.H. Chan Tetrahedron 55 1999 11149 11176
22. B.C. Ranu Eur. J. Org. Chem. 13 2000 2347 2356
23. J. Podlech, and T.C. Maier Synthesis 2003 633 655
24. V. Nair, S. Ros, C.N. Jayan, and B.S. Pallai Tetrahedron 60 2004 1959 1982
25. S. Kumar, P. Kaur, and V. Kumar Curr. Org. Chem. 9 2005 000
26. L.A. Paquette, and T.M. Mitzel J. Am. Chem. Soc. 118 1996 1931 1937
27. L.A. Paquette, and T.M. Mitzel Tetrahedron Lett. 36 1995 6863 6866
28. L.A. Paquette, G.D. Bennett, M.B. Isaac, and A. Chhatriwala J. Org. Chem. 63 1998 1836 1845
29. L.A. Paquette, and T.M. Mitzel J. Org. Chem. 61 1996 8799 8804
30. L.A. Paquette, T.M. Mitzel, M.B. Isaac, C.F. Crasto, and W.W. Schomer J. Org. Chem. 62 1997 4293 4301
31. P.C. Lobben, and L.A. Paquette J. Org. Chem. 63 1998 6990 6998
32. L.A. Paquette, and P.C. Lobben J. Org. Chem. 63 1998 5604 4616
33. P.C. Lobben, and L.A. Paquette J. Org. Chem. 63 1998 6990 6998
34. L.A. Paquette, and P.C. Lobben J. Am. Chem. Soc. 118 1996 1917 1930
35. R. Cusk, M. Hugener, and A. Vasella Helv. Chim. Acta 71 1988 609
36. S. Steurer, and J. Podlech Eur. J. Org. Chem. 1999 1551 1560
37. Preliminary communication: S. Kumar, P. Kaur, and S.S. Chimni Synlett 2002 573 574
38. L.A. Paquette, and R.R. Rothhaar J. Org. Chem. 64 1999 217 224
39. E.L. Eliel J.D. Morrison Vol. 2 Asymmetric Synthesis 1984 Academic New York 125 126
40. A.R. Chamberlin, R.L. Mulholland, S.D. Kahn, and W.J. Hehre J. Am. Chem. Soc. 109 1987 672 677