2004
DOI: 10.1016/j.tet.2004.09.021
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The facile preparation of alkenyl metathesis synthons

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Cited by 116 publications
(87 citation statements)
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References 36 publications
(42 reference statements)
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“…In this case, DY42 10 was made to react with ethyl chloroacetate in the presence of a catalytic amount of potassium iodide [28]. The resulting ester derivative was hydrolyzed to acid 11, which was converted to 12 following the route described previously (Scheme 3).…”
Section: Materials and Solutionsmentioning
confidence: 99%
“…In this case, DY42 10 was made to react with ethyl chloroacetate in the presence of a catalytic amount of potassium iodide [28]. The resulting ester derivative was hydrolyzed to acid 11, which was converted to 12 following the route described previously (Scheme 3).…”
Section: Materials and Solutionsmentioning
confidence: 99%
“…A Sonogashira coupling 14 between compound 11 and propargyl alcohol 12 afforded compound 10 in 86% yield. Conversion of this alcohol 10 to corresponding bromide was performed using carbon tetrabromide and triphenyl phosphine at room temperature 15,16 to obtain compound 8 in 77% yield. The 1 H NMR analysis of compound 8 showed a singlet at δ 4.39 ppm, characteristic for CH2-Br.…”
Section: Resultsmentioning
confidence: 99%
“…In this investigation, the alkylation of the 3-position was achieved by reacting 17β-estradiol/estrone with chloropropyl-alkylamino group in the presence of potassium carbonate (K 2 CO 3 ) and NaI (catalytic amount) in acetone (method A) to afford the desired compounds in moderate to good yields. This method has also been widely using in the alkylation of phenolic group to afford the desired product in up to 80% yield and is said to involve a Finkelstein reaction, followed by an S N 2 reaction to afford the desired product [34-36]. Compounds 5-8 were purified using silica gel flash column chromatography eluting with mixture of CH 2 Cl 2 -MeOH (9: 1 V/V) to afford the pure analogs between 54-77%, which were characterized using proton ( 1 H) NMR, carbon ( 13 C) NMR and high resolution mass spectra (ESI-MS, Electrospray Ionization) analysis as indicated in the experimental section.…”
Section: Resultsmentioning
confidence: 99%