Enantioselective synthesis of (S)-1,6,7,8,9,9a-hexahydroquinolizin-4-one. Formal synthesis of the lycopodium alkaloids senepodine G and cermizine C

Tetrahedron Asymmetry

Volumn 19, Issue 10, 2008, Pages 1233-1236

  Amat, Mercedes ^a   Griera, Rosa ^a   Fabregat, Robert ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,6,7,8,9,9A HEXAHYDROQUINOLIZIN 4 ONE; ALKALOID DERIVATIVE; CERMIZINE C; QUINOLIZIDINE DERIVATIVE; SENEPODINE G;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL;

EID: 44449152549     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.04.022     Document Type: Article

References (13)

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3. Takatsu N., Ohmiya S., and Otomasu H. Chem. Pharm. Bull. 35 (1987) 891-894
4. For a recent review, see:. Escolano C., Amat M., and Bosch J. Chem. Eur. J. 12 (2006) 8198-8207
5. 3SiCl, MeOH) of the diacid. Konno M., Nakae T., Sakuyama S., Imaki K., Nakai H., and Hamanaka N. Synlett (1997) 1472-1474
6. Stetter H., and Rauhut H. Chem. Ber. 91 (1958) 2543-2548
7. For a discussion of the stereochemical outcome in the reduction of 8a-substituted oxazolopiperidone lactams, see:. Amat M., Bassas O., Llor N., Cantó M., Pérez M., Molins E., and Bosch J. Chem. Eur. J. 12 (2006) 7872-7881 and references cited therein
8. 3 or 9-BBN was less satisfactory from both the chemo- and stereoselectivity standpoints as partial reduction of the ester to alcohol was observed and C-2 epimeric mixtures were obtained.
9. Only one synthesis of this enantiopure lactam has been reported:. Lim S.H., Ma S., and Beak P. J. Org. Chem. 66 (2001) 9056-9062
10. For other syntheses of 7 in the racemic series, see:. Rouden J., Seitz T., Lemoucheux L., and Lasne M.-C. J. Org. Chem. 69 (2004) 3787-3793
11. Grzyb J.A., Shen M., Yoshina-Ishii C., Chi W., Brown R.S., and Batey R.A. Tetrahedron 61 (2005) 7153-7175
12. Chou S.-S.P., and Ho C.-W. Tetrahedron Lett. 46 (2005) 8551-8554
13. For a different approach to enantiopure 4-substituted quinolizidines, see:. Amat M., Llor N., Hidalgo J., Escolano C., and Bosch J. J. Org. Chem. 68 (2003) 1919-1928