Total synthesis of (-)-desoxoprosopinine via the diastereoselective reduction of homochiral2-acyl-N-Boc-oxazolidines

Tetrahedron Letters

Volumn 39, Issue 21, 1998, Pages 3505-3508

  Agami, Claude ^a   Couty, François ^a   Mathieu, Hélène ^a  

^a CNRS   (France)

Author keywords

Alkaloids; Asymmetric synthesis; Oxazolidines

Indexed keywords

DESOXOPROSOPININE; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CHROMATOGRAPHY; DIASTEREOISOMER; ENANTIOMER; HYDROXYLATION; METHODOLOGY; SYNTHESIS;

EID: 0032554992     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00646-7     Document Type: Article

References (16)

1. Agami, C.; Couty, F.; Lequesne, C. Tetrahedron 1995, 51, 4043-4056.
2. Agami, C.; Couty, F.; Mathieu, H. Tetrahedron Lett. 1996, 37, 4000-4002.
3. For previous syntheses of 1 or ent-1, see: a) Takao, K. I.; Nigawara, Y.; Nishino, E.; Takagi, I.; Maeda, K.; Tadano, K. I.; Ogawa, S. Tetrahedron, 1994, 50, 5681-5704.
4. b) Kadota, I.; Kawada, M.; Muramatsu, Y.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 7469-7470 and references cited therein.
5. Khuong-Huu, Q.; Ratle, G.; Monseur, X.; Goutarel, R. Bull. Soc. Chim. Belg. 1972, 81, 425-441.
6. 20: +10.4 for ent-7: Klein, L. L.; Mc. Whorter, W. W.; Ko, S.; Pfaff, K. P.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 7362-7364.
7. 25: +16.9 for ent-8: Mulzer, J.; Angermann, A. Tetrahedron Lett. 1983, 24, 2843-2846.
8. Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H. P. J. Am. Chem. Soc. 1983, 105, 7754-7755.
9. 13C NMR: 14.1, 22.7, 25.1, 25.8, 26.9, 29.3, 29.8, 31.7, 31.9, 51.0, 61.2, 61.3, 62.2, 70.0, 75.8, 79.2, 127.3, 127.5, 127.8, 128.2, 128.3, 128.6, 137.9, 138.6, 140.8.
10. 25: -15.9, mp 89.5°.
11. a) Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 9, 2199-2204.
12. b) Anh, N. T.; Eisenstein, O. Nouv. J. Chem. 1977, 1, 61-70.
13. Poli, G.; Maccagni, E.; Manzoni, L.; Pilati, T.; Scolastico, C. Tetrahedron, 1997, 53, 1759-1776.
14. Frieboes, K. C.; Harder T.; Aulbert, D. Strabriger, C.; Bolte, M.; Hoppe, D. Synlett, 1993, 921-923.
15. a) Toyooka, N.; Yotsui, Y.; Yoshida, Y.; Momose, T. J. Org. Chem. 1996, 61, 4882-4883.
16. b) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575-3584.