Annelation of aromatic oxo compounds

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8277-8280

  Karady, Sandor ^a   Amato, Joseph S ^a   Reamer, Robert A ^a   Weinstock, Leonard M ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030580311     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01936-3     Document Type: Article

References (18)

1. 1. (a) Karady, S.; Amato, J.S.; Reamer, R.A.; Weinstock, L.M. J. Am. Chem. Soc., 1981, 103, 6765.
2. (b) Reider, P.J.; Grabowski, E.J.J. Tetrahedron Lett. 1982, 23, 2293.
3. 2. (a) Kant, J.; Walker, D. G. in The Organic Chemstry of β-Lactams; Georg, G. I., Ed.; VCH Publishers, Inc. New York, 1992; p 179.
4. (b) Encyclopedia of Reagents for Organic Synthesis; Paquette L. A., Ed.; J. Wiley& Sons, Ltd. Sussex , England, 1994; p 3733.
5. 2 ring closure of the type 3 to 4 was first described by Ratcliffe, R.W.; Salzmann, T.N.; Christensen, B.G. Tetrahedron Lett. 1980, 21, 31. The use of the more soluble Rh octanoate was introduced by F.E. Roberts and W.K. Russ of these laboratories. We thank them for samples and procedures.
6. 13C NMR spectra of 7c and 7d were completely analogous to 7a.
7. 5. Taylor, E.C.; Davies, H.M.L. Tetrahedron Lett. 1983, 24, 5453, reported the preparation of the ethyl ester and ring substituted analogs of 8 by another route and that rhodium acetate catalyzed cyclization afforded the ethyl ester analog of 11.
8. 6. For recent reviews see: (a) Tao, Y.; McKervey, A. Chem. Rev. 1994, 94, 1091
9. (b). Adams, J.; Spero, D.M. Tetrahedron Lett. 1991, 47, 1765 .
10. (c). Smith, A.B.; Dieter, R.K. Tetrahedron Lett. 1981, 37, 2407.
11. 7. (a) The ethyl ester and free acid of 10 were described by Taylor, G.A. J. Chem. Soc. Perkins I, 1981, 3132.
12. (b) Tetenbaum, M.T.; Hauser, C.R. J. Org. Chem.1958, 23, 229.
13. 8. The rhodium catalyzed decomposition of 8, utilizing our conditions and the exact procedure described in ref 5, yielded 10 and only 1-2 LC area % of a peak corresponding to 11.
14. 9. Leung-Toung, R.; Wentrup, C. J. Org. Chem. 1992, 57, 4850.
15. 2), 172.4 (COOMe).
16. 7b 139-142 °C).
17. 3).
18. 3 gave NOE enhancement to the -OH and the isolated C-H. These spectral characteristics are analogous to those of 10.