New synthesis of all the four isomers of 2-(2-hydroxypropyl)pyrrolidines via iterative asymmetric dihydroxylation to cause enantiomeric enhancement

Tetrahedron Asymmetry

Volumn 8, Issue 16, 1997, Pages 2801-2810

  Takahata, Hiroki ^a   Kubota, Minoru ^a   Momose, Takefumi ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030885245     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00348-0     Document Type: Article

References (20)

1. (a) Massiot, G.; Delaude, C. In The Alkaloids, ed, by Brossi, A. Academic Press, San Diego, 1986, Vol 27, p. 270.
2. (b) Pinder, A. R. Nat. Prod. Rep. 1992, 17.
3. Fitzgerald, J. S. Aust. J. Chem. 1965, 18, 589.
4. Martin, S. A.; Rovirosa, J.; Gambaro, V.; Castillo, M. Phytochemistry 1980, 19, 2007.
5. Platonava, T. F.; Kuzovkov, A. D. Med. Prom. SSSR 1963, 17, 19.
6. Murahashi, S.; Imada, Y.; Kohno, M.; Kawakami, T. Synlett 1993, 395.
7. Louis, C.; Hootelé, C. Tetrahedron: Asymmetry 1997, 8, 109.
8. An inseparable mixture of 1-4 was synthesized. Shono, T.; Matsumura, Y.; Tsubata, K.; Uchida, K. J. Org. Chem. 1986, 51, 2590.
9. Takahata, H.; Kubota, M.; Momose, T. Tetrahedron Lett. 1997, 38, 3451.
10. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
11. Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785.
12. Kolb, H. C.; Sharpless, K. B. Tetrahedron 1992, 48, 10515.
13. For a review, see: Gololobov, Y. G.; Kasukhin, L.F. Tetrahedron 1992, 48, 1353.
14. 1H NMR of Mosher esters of 1 and 3.
15. 19F NMR of Mosher esters of 2 and 4.
16. Lukes, R.; Kovár, J.; Kloubek, J.; Bláha, K. Collect. Czech. Chem. Commun. 1960, 25, 483.
17. Recently, these alkaloids have been isolated, (a) Kim, J. H.; t'Hart, H.; Stevens, J. F. Phytochemistry 1996, 41, 1319.
18. (b) Schneider, M. J.; Brendze, S.; Montali, J. A. Phytochemistry 1995, 39, 1387.
19. Christen, P. Roberts, M. F.; Phillipson, J. D.; Evans, W. C. Phytochemistry 1993, 34, 1147.
20. Späth, E.; Kittel, F. Ber. 1943, 76, 942.