Polar control of the regioselectivity of hetaryne cycloadditions. Synthesis of ellipticine

Synlett

Volumn , Issue 2, 1998, Pages 157-158

  Teresa Diaz M ^a   Cobas, Agustín ^a   Guitián, Enrique ^a   Castedo, Luis ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

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[No Author keywords available]

Indexed keywords

EID: 26844469055     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (16)

1. a) Gribble, G. W. Synthesis and Antitumor Activity of Ellipticine Alkaloids and Related Compounds in The Alkaloids vol. 39, (Ed. Brossi, A.), Academic Press, New York, 1990, p. 239.
2. (b) Poitier, P. Pure Appl. Chem. 1986, 58, 737.
3. c) Gribble, G. W Synthetic Approaches to the Ellipticine Alkaloids via Metalation and Cycloaddition Chemistry in Advances in Heterocyclic Natural Product Synthesis, (Ed. Pearson, W. H.), JAI Press, 1990, vol. 1, p. 43.
4. Gribble, G. W.; Saulnier, M. G. Heterocycles 1985, 23, 1277.
5. Hewlins, M. J. E.; Oliveira-Campos, A-M.; Shannon, V. R. Synthesis 1984, 289.
6. Sainsbury, M. Synthesis 1977, 437.
7. Barone, R.; Chanon, M. Heterocycles 1981, 16, 1357.
8. May, C.; Moody, C. J. J. Chem. Soc. Perkin Trans. 1, 1988, 247.
9. Gribble, G. W.; Saulnier, M. G.; Sibi, M. P.; Obaza-Nutaitis, J. A. J. Org. Chem. 1984, 49, 4518.
10. Davis, D. A.; Gribble, G. W. Tetrahedron Lett, 1990, 31, 1081.
11. Reinecke, M. Tetrahedron 1982, 38, 427.
12. Himeshima, I.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211.
13. Simchen, G.; Pfletschinger, J. Angew. Chem. Int. Ed. Engl. 1976, 15, 428.
14. 3SCl: calcd., 436.064842; found, 436.065156.
15. M.p. 250-252°C (Lit. 243-250°C, see ref. 3).
16. M.p. 308-31°C (Lit. 312-314°C, see ref. 3).