Selenium dioxide oxidations. III. Oxidation of olefins

Schaefer, John P.; Horvath, B.; Klein, Howard P.

doi:10.1021/jo01271a007

Cited by 34 publications

(20 citation statements)

References 2 publications

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“…Recently, we reported (1) the isolation from the petrol extract of the fruits of Arnorphafruticosa L. (Fabaceae) of 6a,12a-dehydro-u-toxicarol, 1, 6a,12a-dehydrodeguelin, 2, and 7,2' ,4' ,5'-tetramethoxyisoflavone, 6. Extended investigation of the same extract offered additional compounds: tephrosin, 3, 1 1-hydroxytephrosin, 4, (-)-6-hydroxy-6a, 12a-dehydro-utoxicarol, 5,7 ,4'-dimethoxyisoflavone, 7, and 5 ,7-dihydroxy-8geranylfiavanone, 8.…”

Section: Introductionmentioning

confidence: 99%

New Rotenoids inAmorpha fruticosaFruits

Somleva¹,

Ognyanov²

1985

Planta Med

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In addition to the rotenoids and flavonoids already reported for the fruits of Amorpha fruticosa, the known compounds tephrosin, 3, and 7 ,4'-demethoxyisoflavone, 7, as well as the new rotenoids (-)-6hydroxy-6a,12a-dehydro-cz-toxicarol, 5, and 3-O-demetylamorphigeni 13, were also isolated from the same material. Chemical evidence for the correct structure of 5,7-dihydroxy-8-geranylflavanone, 8, is given, too.

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Section: Introductionmentioning

confidence: 99%

New Rotenoids inAmorpha fruticosaFruits

Somleva¹,

Ognyanov²

1985

Planta Med

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“…In order to test this hypothesis, we synthesized the enantiomeric substrate ( S )‐ 2 and performed YerE‐catalyzed carboligation (see the Supporting Information) . Here, the same energy difference between the equatorial and the axial conformers would support the formation of 1 S ,3 S (Figure C).…”

Section: Methodsmentioning

confidence: 99%

Substrate‐Determined Diastereoselectivity in an Enzymatic Carboligation

et al. 2016

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Thiamine diphosphate-dependent enzymes catalyze the formation of C-C bonds, thereby generating chiral secondary or tertiary alcohols. By the use of vibrational circular dichroism (VCD) spectroscopy we studied the stereoselectivity of carboligations catalyzed by YerE, a carbohydrate-modifying enzyme from Yersinia pseudotuberculosis. Conversion of the non-physiological substrate (R)-3-methylcyclohexanone led to an R,R-configured tertiary alcohol (diastereomeric ratio (dr) >99:1), whereas the corresponding reaction with the S enantiomer gave the S,S-configured product (dr>99:1). This suggests that YerE-catalyzed carboligations can undergo either an R- or an S-specific pathway. We show that, in this case, the high stereoselectivity of the YerE-catalyzed reaction depends on the substrate's preference to acquire a low-energy conformation.

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“…In an experiment when 8 was heated at 100°in pyridine in the presence of acetic anhydride compound 11 was formed in almost theoretical yield within 1 hr. In a similar experiment when acetic anhydride was replaced by propionic anhydride the corresponding 5-ethyl-3-(2,3,5-tri-0-acetyl-/3-D-ribofuranosyl)imidazo[4,5-d][l,3]oxazin-7-one (12) was obtained in quantitative yield. These novel nucleosides could provide potential intermediates for the synthesis of 1,2-disubstituted purine nucleosides if treated with the requisite amine.…”

Section: Experimental Section19mentioning

confidence: 98%