Stereochemical change in the lewis acid-promoted reaction of 2-siloxypyrrole derived from (L)-glutamic acid. synthesis of a lactacystin analogue

Heterocycles

Volumn 48, Issue 4, 1998, Pages 635-640

  Uno, Hidemitsu ^a   Mizobe, Noboru ^a   Yamaoka, Youtarou ^a   Ono, Noboru ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000927995     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-98-8123     Document Type: Article

References (16)

1. Recent revews, see a) C. W. Jefford, D. Jaggi, A. W. Sledeski, and J. Boukouvalas, In Studies in Natural Products Chemistry, ed. by Atta-ur-Raman, Elsevier, Amsterdam, 1989; Vol. 3, p. 157;
2. b) G. Casiraghi and G. Rassu, Synthesis, 1995, 607.
3. Recent examples for 2-siloxyfurans: C. Castellari, M. Lombardo, G. Pietropaolo, and C. Trombini, Tetrahedron: Asymmetry, 1996, 7, 1059;
4. T. Bauser, Tetrahedron: Asymmetry, 1996, 7, 981;
5. S. F. Martin and K. J. Barr, J. Am. Chem. Soc., 1996, 118, 3299;
6. for 2-siloxythiophene: G. Rassu, P. Spanu, L. Pinna, F. Zanardi, and G. Casiraghi, Tetrahedron Lett., 1995, 36, 1941;
7. for 2-siloxypyrroles: F. Zanardi, L. Battistini, M. Nespi, G. Rassu, P. Spanu, M. Cornia, and G. Casiraghi, Tetrahedron: Asymmetry, 1996, 7, 1167;
8. I. Baussanne and J. Royer, Tetrahedron Lett., 1996, 37, 1213;
9. G. Poli, S. Ciofi, E. Maccagni, and N. Sardone, Tetrahedron Lett., 1995, 36, 8669;
10. M. Martin and F. Bermejo, Tetrahedron Lett., 1995, 36, 7705.
11. T. Mukaiyama, Organic Reactions, 1982, 28, Chap 3.
12. H. Uno, J. E. Baldwin, I. Churcher, and A. T. Russell, Synlett, 1997, 390.
13. H. Uno, J. E. Baldwin, and A. T. Russell, J. Am. Chem. Soc., 1994, 116, 2139.
14. G. Fenteany, R. F. Standaert, W. S. Lane, S. Choi, E. J. Corey, and S. L. Schreiber, Science, 1995, 268, 726, and references cited therein.
15. 1H NMR. A large up-field shift was observed in the exo-methyl group of anti-14 (δ = 0.55) due to the anisotropic effect of the side chain phenyl group.
16. E. J. Corey and G. A. Reichard, J. Am. Chem. Soc., 1992, 114, 10677.