An efficient procedure for the synthesis of thiophene-containing polycyclic compounds via polyene cyclization promoted by the cross conjugated β-keto ester system

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6501-6504

  Liu, Hsing Jang ^a   Tran, Duong Duc Phi ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC HYDROCARBON; POLYENE; THIOPHENE; THIOPHENE DERIVATIVE;

ARTICLE; CONJUGATION; CYCLIZATION; SYNTHESIS;

EID: 0030866363     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01514-1     Document Type: Article

References (11)

1. Weissberger, A.; Taylor, E. C. Thiophene and its derivatives; Gronowitz, S., Ed.; John Wiley & Sons, Inc.: Toronto, 1985, part IV, pp. 397-478.
2. Liu, H. J.; Sun, D.; Shia, K. S. Tetrahetron Lett. 1996, 37, 8073-8076.
3. 13C), high resolution mass spectra and elemental analysis were obtained for all the new compounds.
4. Walker, P.; Hiebert, J. D. Chem. Rev. 1967, 67, 153-195.
5. Piancatelli, G.; Scettri, A.; D'Auria, M. Synthesis, 1982, 245-258.
6. Chan, Y.; Epstein, W. W. Org. Synth. 1973, 55, 49-52.
7. Liu, H. J.; Ulibarri, G.; Nelson, L. A. K. Can. J. Chem. 1994, 72, 2416-2427.
8. The results from the NOE experiment were found to be similar to those of the corresponding unbrominated compound.
9. See reference 10 and references cited therein for a previous preparation of polycyclic thiophene derivatives via polyene cyclization. In this preparation, the cyclization was promoted by an allylic alcohol moiety. The yields of products were modest (∼50%).
10. Macco, A. A.; de Brouwer, R. J.; Buck, H. M. J. Org. Chem. 1977, 42, 3196-3199.
11. We are grateful to the Natural Sciences and Engineering Research Council of Canada and the University of Alberta for financial support.