Investigation of an Acrylate Lynchpin Approach toward the Synthesis of Stolonidiol

Thomas Barton; Dionicio Siegel

doi:10.1055/s-0032-1316589

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(17): 2770-2778
DOI: 10.1055/s-0032-1316589

paper

Investigation of an Acrylate Lynchpin Approach toward the Synthesis of Stolonidiol

Thomas Barton

Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712, USA, Fax: +1(512)4716835 eMail: dsiegel@cm.utexas.edu

,

Dionicio Siegel*

Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, TX 78712, USA, Fax: +1(512)4716835 eMail: dsiegel@cm.utexas.edu

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Abstract

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Abstract

An acrylate lynchpin approach toward the synthesis of stolonidiol has been investigated. To access the key macrocyclization precursor we adapted the silylcupration reaction of alkynes, facilitating attack of the intermediate vinylcuprate on a trisubstituted epoxide. With all of the required carbons of stolonidiol in place, macrocyclization reactions to provide the 11-membered ring were attempted using either a nickel-mediated cyclization of a bromo aldehyde, intercepting methyl acrylate, or an intramolecular Baylis–Hillman cyclization.

Key words

stolonidiol - epoxides - silylcupration - macrocyclization - acrylate lynchpin approach

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