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Synthesis 2018; 50(03): 651-657
DOI: 10.1055/s-0036-1591516
DOI: 10.1055/s-0036-1591516
paper
Improved Synthesis of Racemate and Enantiomers of Taniguchi Lactone and Conversion of Their C–C Double Bonds into Triple Bonds
Further Information
Publication History
Received: 22 August 2017
Accepted after revision: 09 October 2017
Publication Date:
07 November 2017 (online)
Abstract
cis-2-Butene-1,4-diol was heated with triethyl orthoacetate and p-hydroquinone as catalyst at 170 °C to give racemic Taniguchi lactone. It was converted into diastereomeric amides with (S)-1-phenylethylamine for stereoisomer resolution. The double bonds of (±)-, (R)- and (S)-Taniguchi lactones were brominated and dehydrobrominated in two steps, using at first DBU and then LDA, to deliver the triple bonds.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591516.
- Supporting Information
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