Stereoselective synthesis of the indolizinoindole ring system

Tetrahedron Letters

Volumn 44, Issue 11, 2003, Pages 2335-2337

  Allin, Steven M ^a   Thomas, Christopher I ^a   Allard, James E ^a   Duncton, Matthew ^b   Elsegood, Mark R J ^a   Edgar, Mark ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b OSI Pharmaceuticals   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; INDOLE DERIVATIVE; INDOLIZINO[8,7 B]INDOLE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0037430577     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00250-8     Document Type: Article

References (21)

1. Herbst D.R., Smith H. Chem. Abstr. 75:1971;118297d.
2. Herbst D.R., Smith H. Chem. Abstr. 77:1972;P 34373d.
3. Herbst D.R., Smith H. Chem. Abstr. 75:1971;118297d.
4. Herbst D.R., Smith H. Chem. Abstr. 76:1972;113061h.
5. De La Figuera N., Alkorta I., Garcia-Lopez M.T., Herranz R., Gonzalez-Muniz R. Tetrahedron. 51:1995;7841-7856.
6. Martin-Martinez M., De La Figuera N., Latorre M., Herranz R., Garcia-Lopez M.T., Cenarruzabeitia E., Del Rio J., Gonzalez-Muniz R. J. Med. Chem. 43:2000;3770-3777.
7. For example, see: Din Belle D., Tolvanen A., Lounasmaa M. Tetrahedron. 52:1996;11361-11378.
8. Martin S.F., Chen M.X., Early C.T. Org. Lett. 1:1999;79-81.
9. For example, see: Martin S.F., Clark C.W., Corbett J.W. J. Org. Chem. 60:1995;3236-3242.
10. Allin S.M., Northfield C.J., Page M.I., Slawin A.M.Z. Tetrahedron Lett. 39:1998;4905-4908.
11. Allin S.M., James S.L., Martin W.P., Smith T.A.D. Tetrahedron Lett. 41:2001;3943-3946.
12. Allin S.M., James S.L., Martin W.P., Smith T.A.D., Elsegood M.R.J. J. Chem. Soc., Perkin Trans. 1. 2001;3029-3036.
13. 3 solvent.
14. Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre (CCDC 198533).
15. Bocchi V., Casnati G., Gardini G.P. Tetrahedron Lett. 12:1971;683-684.
16. De La Figuera N., Rozas I., Garcia-Lopez M.T., Gonzalez-Muniz R. J. Chem. Soc., Chem. Commun. 1994;613-614.
17. The absence of an NOE between the protons situated at positions 5 and 11b of product 9 is consistent with the proposed structure. As we were unable to isolate the minor diastereoisomer we were unable to carry out a comparative NOE study. This result is in agreement with related work from our group (Ref. 7b).
18. We were able to perform a set of comparative NOE studies on the separable diastereoisomers of product 10. In the case of the major diastereoisomer, 10, an NOE was observed between protons at positions 3 and 5. In the case of the minor diastereoisomer, no NOE was observed. Both results are in accord with previous results from our group detailing the preparation of 5,6-fused bicyclic lactams (Ref. 11).
19. Allin S.M., Vaidya D.G., James S.L., Allard J.E., Smith T.A.D., McKee V., Martin W.P. Tetrahedron Lett. 43:2002;3661-3663.
20. We were able to perform a set of comparative NOE studies on the separable diastereoisomers of product 11. In the case of the minor diastereoisomer an NOE was observed between protons at positions 6 and 12b. In the case of the major diastereoisomer, 11, no NOE was observed.
21. Frigerio M., Santagostino M., Sputore S., Palmisano G. J. Org. Chem. 60:1995;7272-7276.