Volume 31, Issue 12
Natural Products
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ChemInform Abstract: The Triumph of Zinc: A Short and Highly Efficient Synthesis of the Calyculin C1—C9 Tetraene Building Block by Negishi Coupling.

Petri M. Pihko

Petri M. Pihko

Lab. Org. Chem., Helsinki Univ. Technol., SF-02150 Espoo, Finland

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Ari M. P. Koskinen

Ari M. P. Koskinen

Lab. Org. Chem., Helsinki Univ. Technol., SF-02150 Espoo, Finland

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First published: 09 June 2010

Abstract

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ChemInform Abstract

Based on a highly efficient Negishi coupling of a bismetallic vinylzinc species (derived from trans-1,2-bis(tributylstannyl)ethene (I) by lithiation and transmetalation) with the bromo ester (II), a short and efficient synthesis of the phosphonate (IV), a key building block of the C1—C9 fragment of calyculins, is achieved.

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