Stereoselective synthesis of a novel spiroacetal-dihydropyrone related to auripyrone

Tetrahedron Letters

Volumn 47, Issue 12, 2006, Pages 2025-2028

  Perkins, Michael V ^a   Jahangiri, Saba ^a   Taylor, Max R ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

PYRONE DERIVATIVE;

ACETALIZATION; ALDOL REACTION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDRATION; STEREOCHEMISTRY;

EID: 32644465602     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.045     Document Type: Article

References (17)

1. K. Suenaga, H. Kigoshi, and K. Yamada Tetrahedron Lett. 37 1996 5151
2. The numbering system used for the natural product auripyrone will for consistency be used for the model compound throughout.
3. I. Paterson, and M.V. Perkins Tetrahedron Lett. 33 1992 801
4. I. Paterson, and M.V. Perkins Tetrahedron 52 1996 1811
5. R.A. Sampson, and M.V. Perkins Org. Lett. 4 2002 1655
6. +) 306.2189, found 306.2194.
7. 13C NMR signals at δ = 19.6 and 30.1 ppm
8. B.M. Trost, and C.G. Caldwell Tetrahedron Lett. 22 1981 4999
9. E.J. Corey, and P.B. Hopkins Tetrahedron Lett. 23 1982 4871
10. B.M. Trost, C.G. Caldwell, E. Murayama, and D. Heissler J. Org. Chem. 48 1983 3252
11. Aldehyde 15 was rather unstable and partly decomposed upon chromatography and storage. The best results were obtained when freshly prepared aldehyde was used in the subsequent reaction.
12. D.A. Evans, J.S. Clark, R. Metternich, V.J. Novak, and G.S. Sheppard J. Am. Chem. Soc. 112 1990 866
13. D.A. Evans, F. Urpí, T.C. Somers, J.S. Clark, and M.T. Bilodeau J. Am. Chem. Soc. 112 1990 8215
14. D.A. Evans, D.L. Rieger, M.T. Bilodeau, and F. Urpi J. Am. Chem. Soc. 113 1991 1047
15. The aldol condensation between the aldehyde 15 and the Ti(IV) enolate of the unprotected β-hydroxy ketone 17 by the methodology reported by G.P. Luke, and J. Morris J. Org. Chem. 60 1995 3013 produced varied results. Thus the preferred procedure used the protected ketone 18 as described
16. Crystallographic data (excluding structure factors) for the structures 3 and 20 in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 289593 and CCDC 289592, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0) 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk ].
17. W.R. Roush J. Org. Chem. 56 1991 4151