Enantioselective synthesis of trans-fused bicyclo[5.3.0]decane systems via a tandem [4+3] cycloaddition-Nicholas reaction

Tetrahedron Letters

Volumn 40, Issue 35, 1999, Pages 6499-6502

  Montaña, Ángel M ^a   Fernández, David ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

4+3 cycloaddition; Enantioselective synthesis; Nicholas reaction; Pseudoguaiane

Indexed keywords

DECANE;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; ENANTIOMER; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033609781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01336-2     Document Type: Article

References (33)

1. a) Fraga, B.M. Nat. Prod. Rep. 1998, 15, 73;
2. b) Fraga, B.M. Nat. Prod. Rep. 1992, 9, 217.
3. a) Kupchan, S.M.; Eakin, A.; Thomas, A.M. J. Medical Chem. 1971, 14, 1147.
4. b) Chuang, L.F.; Kung, H.F.; Israel M.; Chuang, R.Y. Biochem, Pharmacol Toxicol. 1992, 43, 865;
5. c) Evans, F.J.; Parker, P.J.; Olivier, A.R.; Thomas, S.; Ryves, W.J.; Evans, A.T.; Gordge, P.; Sharwa, P. Biochem. Soc. Trans. 1995, 19, 397.
6. a) Apsimon, J. The Total Synthesis of Natural Products, Vol. 5, John Wiley, New York, 1982, pp. 332-53 7.
7. b) Vandewalle, M.; De Clercq, P. Tetrahedron, 1985, 41, 1767;
8. c) Jennisken, L.H.D.; Wijnberg, J.B.P.A.; De Groot A. Stud. Nat. Prod. Chem. 1994, 14, 355;
9. d) Heathcock, C.H.; Del Mar, E.G.; Graham, S.L. J. Am. Chem. Soc. 1982, 104, 1907.
10. a) Montaña, A.M.; Nicholas, K.M.; Khan, M.A. J. Org. Chem. 1988, 53, 519 3.
11. b) Montaña, A.M.; Nicholas, K.M. J. Org. Chem. 1990, 55, 1569;
12. c) Sugita, K.; Shigeno, K.; Neville, C.F.; Sasai, H.; Shivasa, K.M. Synlett 1994, 326;
13. d) Wender, P.A.; McDonald, F.E. J. Am. Chem. Soc. 1990, 112, 4956;
14. e) Wender, P.A.; Kogen, H.; Lee, H.; Munger J.D.; Wilhelm, R.S.; Williams, P.D. J. Am. Chem. Soc. 1989, 111, 8957.
15. a) Quinkert, G.; Schmalz, H.; Walzar, E.; Kowalczyck, T.; Dürner, G.; Bats, J.W. Angew. Chem. Int., Ed. Engl., 1987, 26, 6 1.
16. b) Thomas, M.; Wong, M.K.C. Tetrahedron 1996, 52, 6307;
17. c) Ohsuka, M.; Takekawa, Y.; Shisido, K. Tetrahedron Lett. 1998, 39, 5803.
18. d) Honda, T.; Ishige, H.; Nagase, H. J. Chem. Soc. Perkin Trans I 1994, 22, 3305.
19. e) Minnaard, A. J. Org. Chem. 1997, 62, 7346;
20. f) Shimoma, F. J. Org. Chem. 1998, 63, 920.
21. a) Hoffmann, H.M.R. Angew Chem. 1973, 85, 87 7;
22. b) Mann, J. Tetrahedron 1986, 42, 4611;
23. c) Rigby, J.H.; Pigge, F.C. Org. React. 1997, 51, 351-478.
24. Nicholas, K.M., Acc. Chem. Res., 1987, 20, 207.
25. Ashcroft, M.R.; Hoffmann, H.M.R. Org. Synth. 1978, 58, 17.
26. a) Majewski, M.; Zheng, G. Syntett, 1991, 173;
27. b) Bunn, B.J.; Simpkins, N.S. J. Org. Chem. 1993, 58, 533;
28. c) Williard, P.G.; Liu, Q.X. J. Am. Chem. Soc. 1993, 115, 3380.
29. Oxford Asymmetry, UK. (-)-(S,S)-1,1′-dimethyldibenzylamine hydrocloride, Ref. 90063; (+)-(R,R)-enantiomer Ref. 90021.
30. Overberger, C.G.; Marullo, N.P.; Hiskey, R.G. J. Am. Chem Soc. 1961, 83, 1374.
31. Varghese, V.; Saha, M.; Nicholas, K.M. Org. Synth. 1988, 67, 141.
32. Le Coq, A.; Gorgues, A. Org. Synth. 1980, 59, 10.
33. Bott, R.W.; Eaborn, C.; Walton, D.R.M. J. Chem. Soc. 1965, 384.