Stereoselective syntheses of (-)-tetrahydrolipstatin via Prins cyclisations

Tetrahedron Letters

Volumn 47, Issue 29, 2006, Pages 4995-4998

  Yadav, J S ^a   Reddy, M Sridhar ^a   Prasad, A R ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Anti obesity; Homoallylic alcohol; Prins cyclisation and allylic cleavage

Indexed keywords

TETRAHYDROLIPSTATIN;

ALKYLATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; EPOXIDATION; OXIDATIVE STRESS; STEREOCHEMISTRY;

EID: 33744966868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.05.116     Document Type: Article

References (44)

1. Weibel E.K., Hadvary P., Hochuli E., Kupfer E., and Lengsfeld H. J. Antibiot. 40 (1987) 1081-1085
2. Hochuli E., Kupfer E., Maurer R., Meister W., Mercadal Y., and Schmidt K. J. Antibiot. 40 (1987) 1086-1091
3. Barbier P., Schneider F., and Widmer U. Helv. Chim. Acta 70 (1987) 1412-1418
4. Barbier P., Schneider F., and Widmer U. Helv. Chim. Acta 70 (1987) 196-202
5. Barbier P., and Schneider F. J. Org. Chem. 53 (1988) 1218-1221
6. Dirat O., Kouklovsky C., and Langlois Y. Org. Lett. 1 (1999) 753-755
7. Ghosh A.K., and Liu C. Chem. Commun. (1999) 1743-1744
8. Paterson I., and Doughty V.A. Tetrahedron Lett. 40 (1999) 393-394
9. Wedler C., Costisella B., and Schick H. J. Org. Chem. 64 (1999) 5301-5303
10. Parsons P.J., and Cowell J.K. Synlett (2000) 107-109
11. Ghosh A.K., and Fidanze S. Org. Lett. 2 (2000) 2405-2407
12. Bodkin J.A., Humphries E.J., and McLeod M.D. Aust. J. Chem. 56 (2003) 795-803
13. Bodkin J.A., Humphries E.J., and McLeod M.D. Tetrahedron Lett. 44 (2003) 2869-2872
14. Thadani A.N., and Batey R.A. Tetrahedron Lett. 44 (2003) 8051-8055
15. Polkowska J., Lukaszewicz E., Kiegiel J., and Jurczak J. Tetrahedron Lett. 45 (2004) 3873-3875 and references cited therein
16. Barry C.St.J., Crosby S.R., Harding J.R., Hughes R.A., King C.D., Parker G.D., and Willis C.L. Org. Lett. 5 (2003) 2429-2432
17. Yang X.-F., Mague J.T., and Li C.-J. J. Org. Chem. 66 (2001) 739-747
18. Yadav J.S., Reddy B.V.S., Sekhar K.C., and Gunasekar D. Synthesis 6 (2001) 885-888
19. Yadav J.S., Reddy B.V.S., Reddy M.S., and Niranjan N. J. Mol. Catal. A: Chem. 210 (2004) 99-103
20. Yadav J.S., Reddy B.V.S., Reddy M.S., Niranjan N., and Prasad A.R. Eur. J. Org. Chem. (2003) 1779-1783
21. Rychnovsky S.D., and Powell N.A. J. Org. Chem. 62 (1997) 6460-6461
22. Obringer M., Colobert F., Neugnot B., and Solladie G. Org. Lett. 5 (2003) 629-633
23. BouzBouz S., and Cossy J. Org. Lett. 2 (2000) 501-504
24. Rychnovsky S.D. Chem. Rev. 95 (1995) 2021-2040
25. Yet L. Chem. Rev. 103 (2003) 4283-4306
26. Dias L.C., de Oliveira L.G., Vilcachagua J.D., and Nigsch F.J. Org. Synth. 70 (2005) 2225-2234
27. Keck G.E., and Truong A.P. Org. Lett. 7 (2005) 2153-2156 and references cited therein
28. Yadav J.S., Reddy M.S., and Prasad A.R. Tetrahedron Lett. 46 (2005) 2133-2136
29. Yadav, J. S.; Reddy, M. S.; Prasad, A. R. Tetrahedron Lett., in press.
30. Yadav, J. S.; Reddy, M. S.; Rao, P. P. Prasad, A. R. Tetrahedron Lett., in press.
31. Bonini C., Chiummiento L., Lopardo M.T., Pullex M., Colobert F., and Solladie G. Tetrahedron Lett. 44 (2003) 2695-2697
32. Furrow M.E., Schaus S.E., and Jacobsen E.N. J. Org. Chem. 68 (1998) 6776-6777
33. Baskaran S., and Chandrasekaran S. Tetrahedron Lett. 31 (1990) 2775-2778
34. Ali S.M., Ramesh K., and Borchardt R.T. Tetrahedron Lett. 31 (1990) 1509-1512
35. Frater G. Helv. Chim. Acta 62 (1979) 2825-2828
36. Frater G., Muller U., and Gunther W. Tetrahedron 40 (1984) 1269-1277
37. Naito H., Kawahara E., Maruta K., Maeda M., and Sasaki S. J. Org. Chem. 60 (1995) 4419-4427
38. Fuji K., Kawabata T., and Fujita E. Chem. Pharm. Bull. 28 (1980) 3662-3664
39. Mitsunobu O. Synthesis (1981) 1-28
40. -1.
41. Keck G.E., Tarbet K.H., and Geraci L.S. J. Am. Chem. Soc. 115 (1993) 8467-8468
42. Hon Y.S., Lu L., and Li S.Y. J. Chem. Soc., Chem. Commun. (1990) 1627-1628
43. Gao Y., Hanson R.M., Klunder J.M., Ko S.Y., Masamune H., and Sharpless K.B. J. Am. Chem. Soc. 109 (1987) 5765-5780
44. Vatele J.-M. Tetrahedron Lett. 47 (2006) 715-718