Preparation of a chiral azadiene for the synthesis of 5-aza analogues of angucyclinones

Tetrahedron Letters

Volumn 52, Issue 18, 2011, Pages 2336-2339

  Sissouma, Drissa ^a,b   Dequirez, Geoffroy ^a   Collet, Sylvain ^a   Guingant, André ^a  

^a UNIVERSITÉ DE NANTES   (France)

^b UNIVERSITÉ FÉLIX HOUPHOUËT BOIGNY   (Côte d’Ivoire)

Author keywords

Aza angucyclinone; Chiral azadiene; Enaminone; Ester hydrolysis; Hetero Diels Alder reaction

Indexed keywords

ALKADIENE; ANGUCYCLINONE; DIKETONE; ESTER DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIELS ALDER REACTION; ENANTIOMER; HEATING; SYNTHESIS;

ALNUS;

EID: 79953274157     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.084     Document Type: Article

References (13)

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2. N.Q. Vu, G. Dujardin, S. Collet, E.-A. Raiber, A. Guingant, and M. Evain Tetrahedron Lett. 46 2005 7669 7673
3. A.G. Myers, N.J. Tom, M.E. Fraley, S.B. Cohen, and D.J. Madar J. Am. Chem. Soc. 119 1997 6072 6094
4. 2 140-141 °C).
5. A similar regioselectivity has already been observed for enamination of β-diketones structurally closed to 7. J.E. Foster, J.M. Nicholson, R. Butcher, J.P. Stables, I.O. Edafiogho, A.M. Goodwin, M.C. Henson, C.A. Smith, and K.R. Scott Bioorg. Med. Chem. 7 1999 2415 2425
6. 2 = 0.1317, R = 0.0584 for 3124 reflections with I > 2σ(I). CCDC 799310 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
7. D.F. Taber, J.C. Amedio Jr., and F.J. Gulino Org. Chem. 54 1989 3474 3475
8. Y. Koyama, R. Yamaguchi, and K. Suzuki Angew. Chem., Int. Ed. 47 2008 1084 1087
9. +] 168.1145, found 168.1143.
10. B. Pita, C.F. Masaguer, and E. Raviña Tetrahedron Lett. 41 2000 9829 9833
11. +] 125.0835, found 125.0835.
12. 2). Contamination with (S)-enantiomer is due to the fact that the starting diketone ester 8 was difficult to be obtained in pure form and remained contaminated with some amount of 7 (cf. Ref.3).
13. 3) (ee 88% measured by HPLC analysis on a Chiralcel OJ-H column).