Hydroxylated α-vinylpyrrolidines from sugar-derived 2,5-dihydrofurans. Synthesis of (1S,2S,8aR)-1,2-dihydroxyindolizidine by ring closing olefin methathesis

Synthesis

Volumn , Issue 12, 1997, Pages 1415-1419

  Paolucci, Claudio ^a   Musiani, Lorenzo ^a   Venturelli, Francesca ^a   Fava, Antonino ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Azasugars; Dihydrofurans; Hydroxylated pyrrolidines; Indolizidines; Ring closing olefin metathesis

Indexed keywords

ALKENE; ALPHA VINYLPYRROLIDINE; DIHYDROFURAN; INDOLIZIDINE DERIVATIVE; SUGAR; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; NONHUMAN; SYNTHESIS;

EID: 0031467338     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1361     Document Type: Article

References (51)

1. Elbein, A.D. Ann. Rev. Biochem. 1987, 56, 497.
2. Fleet, W.J. Chem. Brit. 1989, 287.
3. Sinnot, L. Chem. Rev. 1990, 90, 1171.
4. Kibayashi, N. Studies in Natural Product Chemistry, Attaur-Rahman, Ed., Elsevier, Amsterdam, 1992; p. 229.
5. For reviews see: Liddell, J.R. Nat. Prod. Rep. 1996, 13, 187.
6. Robins, J.D. Nat. Prod. Rep. 1995, 12, 413;
7. 1994, 11, 613;
8. 1993, 10, 487;
9. 1992, 9, 313.
10. Michael, J.P. Nat. Prod. Rep. 1995, 12, 535;
11. 1994, 11, 17 and 639;
12. 1993, 10, 51.
13. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 677.
14. Harrison T. Contemporary Organic Synthesis 1995, 2, 209.
15. Casiraghi, G.; Rassu, G. Synthesis 1995, 607.
16. For recent contributions see: Person, W.H.; Hembre, E.J. J. Org. Chem. 1996, 61, 5546.
17. Mulzer, J.; Meier, A.; Buschmann, J.; Luger, P. J. Org. Chem. 1996, 61, 566.
18. Harayama, H.; Okuno, H.; Takahashi, Y.; Kimura, M.; Fugami, K.; Tanaka, S.; Tamaru, Y. Tetrahedron Lett. 1996, 31, 7287.
19. Bolton, G.L. Tetrahedron Lett. 1996, 37, 3433.
20. Chappie, T.A.; Weekly, R.M.; McMills, M.C. Tetrahedron Lett. 1996, 37, 6523.
21. Adams, D.R.; Bailey, P.D.; Collier, I.D.; Heffernan, J.D.; Stokes, S. Chem. Commun. 1996, 349.
22. Fry, D.F.; Brown, M.; McDonald, J.C. Tetrahedron Lett. 1996, 37, 6227.
23. Goti, A.; Cardona, F.; Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron Asymmetry 1996, 7, 1659.
24. Bell, A.A.; Pickering, L.; Watson, A.A.; Nash, R.J.; Griffiths, R.C.; Jones, M.J.; Fleet, G.W.J. Tetrahedron Lett. 1996, 37, 8561.
25. Davis, B.; Bell, A.A.; Nash, R.J.; Watson, A.A.; Griffiths, R.C.; Jones, M.J.; Smith, C.; Fleet, G.W.J. Tetrahedron Lett. 1996, 37, 8565.
26. Shilvock, J.P.; Weatley, J.R.; Davis, B.; Nash, R.J.; Griffiths, R.C.; Jones, M.J.; Muller, M.; Crook, S.; Watkin, D.J.; Smith, C.; Besra, G.S.; Brennan, P.J., Fleet, G.W.J. Tetrahedron Lett. 1996, 37, 8569.
27. Murray, A.; Proctor, G.R.; Muray, P.J. Tetrahedron 1996, 52, 3757.
28. Bremner, J.B.; Skelton, B.W.; Smith, R.J.; Tarrant, G.J.; White, A.H. Tetrahedron Lett. 1996, 37, 8573.
29. Huang, Y.; Dalton, D.R.; Carrol, J.P. J. Org. Chem. 1997, 62, 372.
30. Denmark, S.E.; Parker, Jf., D.L.; Dixon, J.A. J. Org. Chem. 1997, 62, 435.
31. Barili, P.L.; Berti, G.; Cateleni, G.; D'Andrea, F.; De Rensis, F.; Puccioni, L. Tetrahedron 1997, 53, 3407.
32. Kang, S.H.; Ryu, D.H. Tetrahedron Lett. 1997, 38, 607.
33. Cerè, V.; Mazzini, C.; Paolucci, C.; Pollicino, S.; Fava, A. J. Org. Chem. 1993, 58, 4567.
34. Paolucci, C.; Mazzini, C.; Fava, A. J. Org. Chem. 1995, 60, 169.
35. Paolucci, C.; Venturelli, F.; Fava, A. Tetrahedron Lett. 1995, 36, 8127.
36. Preliminary observations from this laboratory, however, indicate that when the electrophilic fragment in B is PhSe (arising from benzeneselenenyl phthalimide promoted cyclization) concerted thermal elimination of the selenoxide occurs exclusively towards the enol ether D.
37. Brandi, A.; Cicchi, S.; Cordero, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806.
38. Giovannini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem. 1995, 60, 5706.
39. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398.
40. Sakai, N.; Ohfune, Y. J. Am. Chem. Soc. 1992, 114, 998.
41. Schwab, P.; Grubbs, R.H.; Ziller, J.W. J. Am. Chem. Soc. 1996, 118, 100. Our catalyst was a commercial sample purchased from Strem Chemicals.
42. Grubbs, R.H.; Miller, S.J.; Fu, G.C. Acc. Chem. Res. 1995, 28, 446.
43. Fu, G.C.; Grubbs, R.H. J. Am. Chem. Soc. 1992, 114, 7324.
44. Martin, S.F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M.N. Tetrahedron Lett. 1994, 35, 6005.
45. Martin, S.F.; Chen, H.-J.; Curtney, A.K.; Liao, Y.; Patzel, M.; Ramser, M.N.; Wagman, A.S. Tetrahedron 1996, 52, 7251.
46. Overkleft, H.S.; Pandit, U.K. Tetrahedron Lett. 1996, 37, 547.
47. Schuster, M.; Pernerstorfer, J.; Blechert, S. Angew. Chem. 1996, 108, 2111;
48. Angew. Chem. Int. Ed. Engl. 1996, 35, 1979.
49. Huwe, C.H.; Blechert, S. Synthesis 1997, 61.
50. Shon, Y.-S.; Lee, T.R. Tetrahedron Lett. 1997, 378, 1283.
51. Along with the main RCM product a side product (≈10%) was also formed whose NMR spectra suggest it to be an isomer of the starting material where the double bond in the N-acyl moiety had migrated to the conjugate position.