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Convergent Total Syntheses of Callipeltosides A, B, and C

Authors


  • We gratefully acknowledge Novartis (J.R.F.), the EPSRC (C.M.P., T.N.S. and R.A.B.) and the B.P. 1702 Professorship endowment (S.V.L.) for generous funding. We also thank Dr. R. Turner, Dr. J. Davies and D. Howe for HPLC assistance, X-ray crystallography and NMR experiments, respectively.

Abstract

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Going for the hat-trick: The synthesis of the entire callipeltoside family of natural products is described. Key to this synthesis was the coupling of the di-ene-yne and pyran fragments by a diastereoselective alkenylzinc addition allowing rapid access to the common aglycon. Attachment of each relevant L-configured sugar resulted in the first total synthesis of callipeltoside B (see scheme), and the syntheses of callipeltosides A and C.

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