2021
DOI: 10.1002/chir.23390
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Absolute configuration assignment of stigmasterol oxiranes

Abstract: Diastereoisomeric stigmasterol oxiranes 4, 5, 8, and 9 are known phytosterol oxidation products (POPs) that have been evaluated for their cytotoxicity, although the results are of limited significance since, in most cases, they were evaluated as mixtures. Consequently, to establish biological activity hierarchy of these oxides, it is critical to evaluate individual pure POPs. Therefore, we now describe the obtention of individual molecules and their absolute configuration (AC) determination. The two acetylated… Show more

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Cited by 2 publications
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“…In addition, naturally occurring benzodihydrofurans 1 and 2 were successfully tested 4 as growth inhibitors of the insect species Tenebrio molitor, while the structure of 1 was independently verified 5 in a single-crystal x-ray diffraction (XRD) study. 5 From our three lustrous vibrational circular dichroism (VCD) experience, accumulated since the first study 6 of alkaloids from plants of Chilean origin, through the years during which a few VCD reviews 7,8 were put forward, 9 until current times, 10 it could be expected that the structural attributes of 1 would allow a straightforward AC determination of the molecule. Inspection of the structure of 1 reveals that this C 22 H 20 O 5 compound possesses only 4 sp 3 carbon atoms of which one is a methyl group, a sole stereogenic center which is located at C-2 on a benzodihydrofuran ring system and has an almost rigid p-hydroxycinnamoyl ester group whose phenolic hydroxy group can adopt 2 orientations.…”
Section: Introductionmentioning
confidence: 99%
“…In addition, naturally occurring benzodihydrofurans 1 and 2 were successfully tested 4 as growth inhibitors of the insect species Tenebrio molitor, while the structure of 1 was independently verified 5 in a single-crystal x-ray diffraction (XRD) study. 5 From our three lustrous vibrational circular dichroism (VCD) experience, accumulated since the first study 6 of alkaloids from plants of Chilean origin, through the years during which a few VCD reviews 7,8 were put forward, 9 until current times, 10 it could be expected that the structural attributes of 1 would allow a straightforward AC determination of the molecule. Inspection of the structure of 1 reveals that this C 22 H 20 O 5 compound possesses only 4 sp 3 carbon atoms of which one is a methyl group, a sole stereogenic center which is located at C-2 on a benzodihydrofuran ring system and has an almost rigid p-hydroxycinnamoyl ester group whose phenolic hydroxy group can adopt 2 orientations.…”
Section: Introductionmentioning
confidence: 99%