Improved Synthesis of Racemate and Enantiomers of Taniguchi Lactone and Conversion of Their C-C Double Bonds into Triple Bonds

被引：5

作者：

Krizkova, Petra Malova ^{[1
]}

Lindner, Wolfgang ^{[2
]}

Hammerschmidt, Friedrich ^{[1
]}

机构：

[1] Univ Vienna, Inst Organ Chem, Fac Chem, Wahringerstr 38, A-1090 Vienna, Austria

[2] Univ Vienna, Inst Analyt Chem, Fac Chem, Wahringerstr 38, A-1090 Vienna, Austria

来源：

SYNTHESIS-STUTTGART | 2018年 / 50卷 / 03期

关键词：

alkynes; chiral resolution; electrocyclic reaction; halogenation; acetals; lactones; STEREOSELECTIVE TOTAL-SYNTHESIS; DIMETHYL (DIAZOMETHYL)PHOSPHONATE; ABSOLUTE-CONFIGURATION; ALDEHYDES; REAGENT; ALKYNES; GENERATION;

D O I：

10.1055/s-0036-1591516

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

cis-2-Butene-1,4-diol was heated with triethyl orthoacetate and p-hydroquinone as catalyst at 170 degrees 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.

引用

页码：651 / 657

页数：7

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