Complementary routes for the stereoselective synthesis of functionalized benzoquinolizidine targets

Tetrahedron Letters

Volumn 47, Issue 32, 2006, Pages 5713-5716

  Allin, Steven M ^a   Duffy, Liam J ^a   Bulman Page, Philip C ^a   McKee, Vickie ^a   Edgar, Mark ^a   McKenzie, Michael J ^c   Amat, Mercedes ^b   Bassas, Oriol ^b   Santos, Maria M M ^b   Bosch, Joan ^b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF BARCELONA   (Spain)

^c CHARNWOOD MOLECULAR LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLIZIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; RACEMIZATION; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 33745879813     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.035     Document Type: Article

References (15)

1. Battersby A.R., Kapil R.S., Bhakuni B.S., Popli S.P., Merchant J.R., and Salgar S.S. Tetrahedron Lett. (1965) 4965-4971
2. Takacs J.M., and Boito S.C. Tetrahedron Lett. 36 (1995) 2941-2944 and references therein
3. Itoh A., Ikuta Y., Tanahashi T., and Nagakura N. J. Nat. Prod. 63 (2000) 723-725
4. Takayama H., Arai M., Kitajima M., and Aimi N. Chem. Pharm. Bull. 50 (2002) 1141-1143
5. Tan G.T., Kinghorn A.D., Hughes S.H., and Pezzuto J.M. J. Biol. Chem. 266 (1991) 23529-23536
6. For recent examples, see:. Allin S.M., Thomas C.I., Doyle K., and Elsegood M.R.J. J. Org. Chem. 70 (2005) 357-359
7. Bassas O., Llor N., Santos M.M.M., Griera R., Molins E., Amat M., and Bosch J. Org. Lett. 7 (2005) 2817-2820
8. Allin S.M., Khera J.S., Thomas C.I., Witherington J., Doyle K., Elsegood M.R.J., and Edgar M. Tetrahedron Lett. 47 (2006) 1961-1964
9. For related conjugate additions, see:. Amat M., Pérez M., Llor N., Escolano C., Luque F.J., Molins E., and Bosch J. J. Org. Chem. 69 (2004) 8681-8693
10. Allin S.M., Vaidya D.G., James S.L., Allard J.E., Smith T.A.D., McKee V., and Martin W.P. Tetrahedron Lett. 43 (2002) 3661-3663
11. For compounds 7 and 14, a positive NOE effect was observed between the proton at position 11b and a proton of the newly added vinyl substituent. No positive NOE effect was observed between the proton substituents at positions 11b and 2.
12. Amat M., Bassas O., Cantó M., Llor N., Santos M.M.M., and Bosch J. Tetrahedron 61 (2005) 7693-7702
13. -1, F(0 0 0) = 388, 238 least-squares parameters, R1 = 0.0303, wR = 0.0777 (2σ data). CCDC 297432 contains supplementary crystallographic data in cif format. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK. Fax +44 1223 336033, e-mail: deposit@ccdc.cam.ac.uk.).
14. 5 requires 333.1576).
15. Sheldrick, G. M. shelxtl version 6.12, Bruker-AXS, Madison WI, 2001.