Stereoselective radical addition of tertiary amines to (5R)-5- menthyloxy-2[5H]-furanone: Application to the enantioselective synthesis of (-)-isoretronecanol and (+)-labumine

Tetrahedron Letters

Volumn 40, Issue 16, 1999, Pages 3173-3174

  Bertrand, Samuel ^a   Hoffmann, Norbert ^a   Pete, Jean Pierre ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

FURANONE DERIVATIVE; INDOLIZIDINE ALKALOID; PYRROLIZIDINE ALKALOID; TERTIARY AMINE;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; ENANTIOMER; PHOTOREACTIVITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033574691     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00452-9     Document Type: Article

References (12)

1. Bertrand, S.; Hoffmann. N. and Pete. J.P.. preceding paper.
2. a) Nishimura, Y. Studies in Natural Product Chemistry Vol. 1 (Atta-ur-Rahman. ed.). Elsevier, Amsterdam, 1988, 228-303;
3. b) Pearson. W.H. ibid Vol. 1 (Atta-ur-Rahman, ed.), Elsevier, Amsterdam, 1988, 323-358;
4. c) Hudlicky. T.; Rulin, F.; Lovelace, T.C.; Reed, J.W. ibid Vol. 3 (Atta-ur-Rahman, ed.), Elsevier, Amsterdam, 1989. 3-72.
5. Naturally Occurring Pyrrolizidine Alkaloids (Rizk, A.f.m.; Ed.), CRC Press Inc., Boca Raton, 1991.
6. a) Keusenkothen, P.F.; Smith, M.B. J. Chem. Soc., Perkin Trans 1 1994, 2485-2492;
7. b) Haviari. G.; Célérier, J.P.: Petit, H. Lhommet. G. Tetrahedron Lett. 1993, 34, 1599-1600 and ref. cited therein.
8. Flynn, D.L.; Zabrowski. DL.; Becker, D.P.; Nosal, R.; Villamil, C.I.; Gullikson, G.W.; Moumini, C.; Yang, D.C. J. Med. Chem. 1992, 35, 1486-1489 and ref. cited therein.
9. Whitlock, G.A.; Carreira, E.M. J. Org. Chem. 1997, 62, 7916-7917.
10. Santamaria. J.; Ouchabane. R.; Rigaudy. J. Tetrahedron Lett. 1989. 30, 3977-3980.
11. 2 und 3 were enantiomerically pure (>98% ee, chiral gas chromatography, Chrompack, CP-Cyclodextrin-B-236-M-19).
12. 1