Synthetic access to optically active isoflavans by using allylic substitution

Takashima, Yuji; Kaneko, Yuki; Kobayashi, Yuichi

doi:10.1016/j.tet.2009.10.116

Cited by 30 publications

(19 citation statements)

References 52 publications

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“…The 13 C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra of 1 showed 18 carbon signals (Table 2) attributed to 3 × OCH 3 , 2 × CH 2 (one oxygen-bearing), 6 × CH (five aromatic methines), and 7 × C (five oxygenated aromatic carbons). These spectroscopic data indicated that compound 1 was an isoflavane possessing a hydroxy and three methoxy groups [18,19,20]. Comparison of the 1 H and 13 C-NMR data of 1 and sativan [18] suggested that an additional methoxy group was substituted at C-8 in 1 .…”

Section: Resultsmentioning

confidence: 99%

“…These spectroscopic data indicated that compound 1 was an isoflavane possessing a hydroxy and three methoxy groups [18,19,20]. Comparison of the 1 H and 13 C-NMR data of 1 and sativan [18] suggested that an additional methoxy group was substituted at C-8 in 1 . The planar structure of 1 was further confirmed by 2D NMR experiments, including 1 H-detected heteronuclear single quantum coherence (HSQC), 1 H– 1 H correlation spectroscopy ( 1 H– 1 H COSY), and 1 H-detected heteronuclear multiple bond (HMBC) experiments.…”

Section: Resultsmentioning

confidence: 99%

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New Isoflavanes from Spatholobus suberectus and Their Cytotoxicity against Human Breast Cancer Cell Lines

et al. 2019

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The rattans of Spatholobus suberectus Dunn are a traditional Chinese medicine activating blood circulation and removing stasis. They have often been used for the traditional Chinese medicinal treatment of breast cancer in modern China. In this study, four novel isoflavanes (1–3 and 5) and four known analogues (4 and 6–8) were isolated from an ethanolic extract of the rattans of S. suberectus. Their structures were elucidated by extensive spectroscopic analyses and electronic circular dichroism studies. MCF-7 and MDA-MB-231 human breast cancer cell lines were used to evaluate the cytotoxic effects of the isolates. Interestingly, compounds 1 and 2 only inhibited the proliferation of MCF-7 cells, while compound 6 showed a selective cytotoxicity against MDA-MB-231 cells. However, compound 4 had significant cytotoxicity against both MCF-7 and MDA-MB-231 cell lines.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

New Isoflavanes from Spatholobus suberectus and Their Cytotoxicity against Human Breast Cancer Cell Lines

et al. 2019

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“…Next, the phosphonium chloride salt 17 was constructed in 62 % yield from the nonracemic alcohol 16 (99 % ee ) 9. 10 This salt was then combined with benzaldehyde 15 and sodium hexamethyldisilazide to afford the enol ether 12 in 59 % yield as a 2:1 mixture of E and Z isomers 11. Although our many attempts to improve this ratio were futile,12 chromatography gave the pure E isomer in a 37 % overall yield from the starting alcohol 16 .…”

Section: Methodsmentioning

confidence: 99%

Unified Total Syntheses of (−)‐Medicarpin, (−)‐Sophoracarpan A, and (±)‐Kushecarpin A with Some Structural Revisions

2014

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“…By taking a total of 11 steps, the yield of ( S )‐equol improved to 31.6%. Moreover, this strategy has been recognized as an efficient approach to the ( S )‐and ( R )‐isoflavans synthesis (Takashima, Kaneko, & Kobayashi, ). It is noteworthy that the above two approaches to total syntheses require the involvement of 1 equiv chiral auxiliary or chiral starting material.…”

Section: Approaches For Equol Productionmentioning

confidence: 99%

Advances in exploring equol production and application

2019

J Food Process Preserv

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The soybean isoflavone daidzein has been extensively studied. Equol represents the main active metabolite of daidzein in vivo. Due to its broadly biological activities, the preparation and characterization of equol have attracted a great deal of interest. In this review, the focus of attention is placed on the approaches to equol production, including the total synthesis of equol, equol from natural bacteria fermentation and synthetic biology for equol production. It is expected that the industrial production of equol with high yield could be realized in an economic way in the future. In addition, pharmacological activities and clinical applications of equol are also discussed to gain a systematically understanding as to the prospect of development for equol. Practical applications Equol is the main active metabolite of daidzein in vivo and considered to be the most active metabolite of the soybean isoflavones. It has broadly biological activities, including antitumor, antioxidative properties, cardiovascular protection, and relieve menopausal symptoms. However, only 25%–30% of young people can excrete equol in vivo when supplied with soy foods. So, it is necessary to develop efficient methods for equol preparation. Meanwhile, more systematic researches for the pharmacological activity of equol are also required. As mentioned above, this manuscript entitled “Advances in exploring Equol production and application,” hoping that this review should draw widespread attention.

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Synthetic access to optically active isoflavans by using allylic substitution

Cited by 30 publications

References 52 publications

New Isoflavanes from Spatholobus suberectus and Their Cytotoxicity against Human Breast Cancer Cell Lines

New Isoflavanes from Spatholobus suberectus and Their Cytotoxicity against Human Breast Cancer Cell Lines

Unified Total Syntheses of (−)‐Medicarpin, (−)‐Sophoracarpan A, and (±)‐Kushecarpin A with Some Structural Revisions

Advances in exploring equol production and application

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