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DOI: 10.1055/s-2003-36269
Synthesis of the α,β-Unsaturated δ-Lactones (+)-Anhydrocalopin and (+)-Dehydrocalopin
Publication History
Publication Date:
18 December 2002 (online)
Abstract
During our investigations on the calopin group of mushroom metabolites, a synthesis of 3,4-disubstituted α,β-unsaturated δ-lactones has been developed. It was applied to the synthesis of optically active dehydrocalopin (2) and anhydrocalopin (3).
Key words
natural products - δ-lactones - cyclizations - epoxides - Horner-Emmons reaction
- 1
Hellwig V.Dasenbrock J.Gräf C.Kahner L.Schumann S.Steglich W. Eur. J. Org. Chem. 2002, 2895 - 2
Ebel H.Polborn K.Steglich W. Eur. J. Org. Chem. 2002, 2905 - 3
Ebel H.Knör S.Steglich W. Tetrahedron 2003, 59: in press - 5
Nahm S.Weinreb SM. Tetrahedron Lett. 1981, 22: 3815 - 6
Bowman WR.Brown DS.Burns CA.Marples BA.Zaidi NA. Tetrahedron 1992, 48: 6883 - 7
Hasegawa E.Ishiyama K.Kato T.Horaguchi T.Shimizu T.Tanaka S.Yamashita Y. J. Org. Chem. 1992, 57: 5352 - 8
Snieckus V. Chem. Rev. 1990, 90: 879 - 9
Luke GP.Morris J. J. Org. Chem. 1995, 60: 3013 - 10
Cooke MP.Biciunas KP. Synthesis 1981, 283 - 11
Blanchette MA.Choy W.Davis JT.Essenfeld AP.Masamune S.Roush WR.Sakai T. Tetrahedron Lett. 1984, 25: 2183 - 12
Rathke MW.Nowak M. J. Org. Chem. 1985, 50: 2624 - 13
Adam W.Hadjiarapoglou L.Smerz A. Chem. Ber. 1991, 124: 227 - 14
Adam W.Bialas J.Hadjiarapoglou L. Chem. Ber. 1991, 124: 2377 - 15
Sheldrick GM. SHELXS-86, Program for the Solution of X-ray Structures Universität Göttingen; Germany: 1986. - 16
Sheldrick GM. SHELXL-93, Program for Crystal Structure Refinement Universität Göttingen; Germany: 1993.
References
The numbering of the described δ-lactones follows that of the calopins. [1]
17Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-195296. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336-033; E-mail: deposit@ccdc.cam.ac.uk].