Oxidation of carene by thallium(III) acetate

Ratner, V. V.; Isaeva, Z. G.; Povodyreva, I. P.; Goryachkina, N. F.; Efremov, Yu. Ya.; Arbuzöv, B. A.

doi:10.1007/bf00954285

Cited by 3 publications

(4 citation statements)

References 7 publications

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“…The residue was separated on a column with 17 g of SiO 2 , with a gradient of EtOAc in hexane from 0% to 100% as eluent, to get 0.192 g (1.14 mmol, 12%) of (1 S ,2 R ,6 S )- 1 ([α] D 29 −90.1 ( c 6.07, CHCl 3 ), 93% ee). The spectral data of (1 S ,2 R ,6 S )- 1 corresponded to those described in the literature …”

Section: Methodssupporting

confidence: 63%

“…The spectral data of (1S,2R,6S)-1 corresponded to those described in the literature. 40 (1R,2S,6R)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2diol (1R,2S,6R)-1. Similar to the synthesis of (1S,2R,6S)-1, 0.278 g (1.65 mmol, 17%) of (1R,2S,6R)-1 ([R] D 22 þ87.9 (c 1.70, CHCl 3 ), 98% ee) was obtained from 1.50 g (9.87 mmol) of (þ)-trans-verbenol (þ)-7.…”

Section: ' Experimental Sectionmentioning

confidence: 99%

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Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson’s Disease

et al. 2011

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(1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol 1 possesses potent antiparkinsonian activity in both MPTP and haloperidol animal models. The use of compound 1 resulted in nearly full recovery of the locomotor and exploratory activities and was as effective as the comparator agent (levodopa). All eight stereoisomers of compound 1 have been synthesized and the influence of the absolute configuration on the antiparkinsonian activity of compound 1 was shown.

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Section: Methodssupporting

confidence: 63%

Section: ' Experimental Sectionmentioning

confidence: 99%

Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson’s Disease

et al. 2011

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“…357 Photolysis of the acetyl derivative (349) gives a mixture of (350) and (351). If the irradiation is through a Corex filter, and (349) is in solution in acetone, the products are the cyclopentenes (352) and (353). 358 Photolysis of the methoxy-ketone (354), in ethanol solution, gives the cleavage product (359, while its epimer (356) yields (357) and (358), which are the known irradiation products of cis-caran-4-one (359).…”

Section: Caranesmentioning

confidence: 99%

“…357 Treatment of (346) with trifluoroacetic acid gives carvenone together with the ester (347), and toluene-psulphonic acid in refluxing benzene converts (346) into carvenone and the isomeric ketone (348).357 Photolysis of the acetyl derivative (349) gives a mixture of (350) and (351). If the irradiation is through a Corex filter, and (349) is in solution in acetone, the products are the cyclopentenes (352) and (353).358 Photolysis of the methoxy-ketone (354), in ethanol solution, gives the cleavage product (359, while its epimer (356) yields ( 357) and (358), which are the known irradiation products of cis-caran-4-one (359). 359 The hydrogenation of the unsaturated alcohol (360) over palladized charcoal at 80°C to yield (361)- (363) has been described.360 Treatment of the allylic chloride (364) with KOH gives a low yield of the caradiene (365).…”

Section: Fenchanesmentioning

confidence: 99%