A concise enantioselective synthesis of (+)-α-conhydrine

Heterocycles

Volumn 66, Issue 1, 2005, Pages 107-109

  Nagata, Kazuhiro ^a   Toriizuka, Yosuke ^a   Itoh, Takashi ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646893274     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-05-s(k)44     Document Type: Article

References (16)

1. Casiraghi G., Zanardi F., Rassu G., and Sanu P. Chem. Rev. 95 (1995) 1677
2. Wertheim T. Liebigs Ann. Chem. 100 (1856) 328
3. Ratovelomanana V., Royer J., and Husson H.P. Tetrahedron Lett. 26 (1985) 3803
4. Masaki Y., Imaeda T., Nagata K., Oda H., and Itoh A. Tetrahedron Lett. 30 (1989) 6395
5. Comins D.L., and Williams A.L. Tetrahedron Lett. 41 (2000) 2839
6. Guerreiro P., Ratevelomanana-Vidal V., and Genet J.P. Chirality 12 (2000) 408
7. Agami C., Couty F., and Rabasso N. Tetrahedron 57 (2001) 5393
8. Enders D., Nolte B., Raabe G., and Runsink J. Tetrahedron: Asymmetry 13 (2002) 285
9. Kandula S.V., and Kumar P. Tetrahedron Lett. 44 (2003) 1957
10. Pandey S.K., and Kumar P. Tetrahedron Lett. 46 (2005) 4091
11. Galinovsky F., and Mulley H. Monatsh. Chem. 79 (1948) 426
12. Faber K. Biotransformation in Organic Chemistry (2004), Springer-Verlag, Berlin
13. Uenishi J., Hiraoka T., Hata S., Nishiwaki K., and Yonemitsu O. J. Org. Chem. 63 (1998) 2481
14. Enantiomeric excess of 4 was determined, after converting to the corresponding t-butyldimethylsilyl ether, by HPLC analysis using a chiral column (DAICEL Chiralcel OD) with hexane/2-propanol=200 as the solvent system. Compound 3 was hydrolyzed to afford 4, then enantiomeric excess was determined.
15. Blough B.E., and Carroll F.I. Tetrahedron Lett. 45 (1993) 7239
16. 3) δ 10.5, 24.3, 25.0, 25.4, 26.3, 47.0, 60.2, 75.7.