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Issue 20, 1997
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Displacement of bridgehead sulfonate esters with organometallic reagents: synthesis of 13-alkylated gibberellins

Abstract

Gibberellin A3 is converted to 13-methyl GA4 in nine steps and 58% overall yield. A key step in the synthesis is the substitution of a bridgehead sulfonate ester by an alkyl group. A series of organometallic reagents have been investigated to effect this transformation; optimal yields are obtained from reaction of a methanesulfonate with a Gilman-type organocuprate in diethyl ether, in the presence of boron trifluoride–diethyl ether, thus enabling a variety of bridgehead substituents to be introduced in good to excellent yield.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1997, 2989-2996
Article type
Paper

Displacement of bridgehead sulfonate esters with organometallic reagents: synthesis of 13-alkylated gibberellins

M. Penny, S. M. Westaway and C. L. Willis, J. Chem. Soc., Perkin Trans. 1, 1997, 2989
DOI: 10.1039/A703587J

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