2018
DOI: 10.24820/ark.5550190.p010.451
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Overview of enterolactone biological properties and total synthesis

Abstract: Dedicated to Prof. Gordon Gribble on the occasion of his retirement and for his outstanding contributions to science and mentoring of students.Received 12-23-2017 Accepted 02-17-2018 Published on line 03-04-2018 AbstractLignans are a class of compounds found in plants, especially fiber-rich foods such as flax seeds, whole grains, berries and vegetables. A diet rich in lignans is believed to be protective against cancer, inflammation, viral infection, stroke, and cardiovascular diseases. Enterolactone, a mammal… Show more

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Cited by 3 publications
(6 citation statements)
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“…1 H NMR spectra were recorded on JEOL JNM-ECA600 NMR or Bruker Avance III 700 NMR spectrometer. 13 ESI mass spectra were recorded on a THERMO LTQ Orbitrap XL spectrometer. CSI mass spectra were recorded on a Bruker micrOTOF II spectrometer with cryospray unit.…”
Section: ■ Experimental Sectionmentioning
confidence: 99%
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“…1 H NMR spectra were recorded on JEOL JNM-ECA600 NMR or Bruker Avance III 700 NMR spectrometer. 13 ESI mass spectra were recorded on a THERMO LTQ Orbitrap XL spectrometer. CSI mass spectra were recorded on a Bruker micrOTOF II spectrometer with cryospray unit.…”
Section: ■ Experimental Sectionmentioning
confidence: 99%
“…After being stirred at 30 °C for 15 min, solvent was removed by evaporation under reduce pressure. The crude product was purified by C-2 silica chromatography (ether/hexane = 1/2) to give the desired product (25.4 mg, 92%) as a colorless oil: 1 H NMR (600 MHz, CDCl 3 ) δ 4.48 (dd, J = 8.9, 7.6 Hz, 1H), 3.96 (t, J = 8.9 Hz, 1H), 3.52 (dd, J = 10.7, 5.2 Hz, 1H), 3.47−3.43 (m, 2H), 3.31 (dd, J = 11.0, 6.9 Hz, 1H), 2.75−2.66 (m, 2H); 13 (−)-Enterolactone (3). A catalytic amount of iodine (6.6 mg, 0.026 mmol) was added to a suspension of activated zinc dust (16.9 mg, 0.259 mmol) in DMF (0.1 mL) in a Schlenk tube.…”
Section: ■ Experimental Sectionmentioning
confidence: 99%
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