The Reaction of Isoprene with t-Butyl Hypochlorite in Hydroxylic Solvents

Oroshnik, William; Mallory, Robert A.

doi:10.1021/ja01166a076

Cited by 45 publications

(15 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1. The Z9GOG side chain ( N ‐[( E )‐4‐ t ‐butoxy‐3‐methylbut‐2‐enyl]phthalimide (1a) was prepared as described previously (Orosnik and Mallory 1950, Corse and Kuhnle 1972, Hanuš et al 2000). Acidolysis of the t ‐butyl group of 1a with trifluoroacetic acid was accompanied by O ‐trifluoroacetylation of 1b.…”

Section: Resultsmentioning

confidence: 99%

“…A solution containing 1a (Orosnik and Mallory 1950, Corse and Kuhnle 1972, Hanuš et al 2000) (1 g, 3.6 mmol) in 10 ml dry trifluoroacetic acid was left to stand at room temperature for 16 h. After evaporation of the acid under reduced pressure, the mixture of 1b and its O ‐trifluoracetyl derivative was dissolved in 15 ml of methanol and the solution triturated slowly with 0.2–0.5 equivalents of sodium methanolate in methanol. Hydrolysis of the trifluoroacetate was monitored using TLC (system A; 1b: R f 0.15, O ‐trifluoroacetate of 1b: R f 0.75).…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

New cytokinin metabolites in IPT transgenic Arabidopsis thaliana plants

Werner

Hanuš

Holub

et al. 2003

Physiologia Plantarum

View full text Add to dashboard Cite

Two novel cytokinin metabolites were identified in transgenic Arabidopsis thaliana (L.) Heynh. plants containing the bacterial IPT gene under the transcriptional control of a heat-regulated promoter. After cyclic heat-shock treatment, the endogenous cytokinin concentrations were elevated up to 100-fold compared to the wild-type plants. More then 20 different cytokinin metabolites were found, with zeatin-type cytokinins being the most abundant. The metabolic inactivation of these compounds occurred predominantly through N-glucosylation. No significant accumulation of isopentenyladenine-type cytokinins, and only a small increase in dihydrozeatin metabolites, was observed. Subsequent studies of the abundant, unidentified conjugates revealed the presence of zeatin and dihydrozeatin diglucoside conjugates. Structural analysis, utilizing electrospray-liquid tandem mass spectrometry, identified these as a zeatin-O-glucoside-9-glucoside and dihydrozeatin-O-glucoside-9-glucoside, respectively. A third unknown metabolite, was tentatively identified as a phosphorylated form of zeatin-9-glucoside. The biological activity of these compounds in three cytokinin bioassays was low. A comparison of the cytokinin pattern in transgenic and wild-type plants indicates that these specific metabolites accumulate as a consequence of enhanced cytokinin biosynthesis, and are probably involved in the homeostatic mechanisms that control endogenous cytokinin levels.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

New cytokinin metabolites in IPT transgenic Arabidopsis thaliana plants

Werner

Hanuš

Holub

et al. 2003

Physiologia Plantarum

View full text Add to dashboard Cite

show abstract

“…[16] 1.15 mmol), KH 2 PO 4 (42 mg, 0.31 mmol) and NaBr (12 mg, (E)-4,4-Dimethoxy-2-methyl-2-butenal (16): tert-Butyl hypo-0.115 mmol) were added to a solution of 18 (229 mg, 1 mmol) in chlorite (17.3 g, 0.16 mol) was added at 0°C to a solution of iso-DMSO (8 mL) The solution was stirred for 18 h at 80°C, poured prene (11) (13.6 g, 0.2 mol) in acetic acid (58 g, 0.96 mol). [17] The into water (100 mL) and extracted with chloroform followed by the reaction mixture was stirred for 1 h, hydrolyzed and extracted with standard workup. The residue purified by chromatography (silica petroleum ether.…”

Section: (E)-4-acetoxy-2-methyl-2-butenal (17)mentioning

confidence: 99%

New Retinoid Analogs from δ-Pyronene, a Natural Synthon

et al. 1999

View full text Add to dashboard Cite

show abstract

“…Neither Petrov (11) nor Oroshnik (12) could reproduce these experiments. Oroshnik (12) and Mallory did react t-butyl hypochlorite with isoprene in acetic acid as a solvent and obtained in 20-30% yield the wanted E-isomer. Allais (13) as well as Babler (14) and Buttner also carried out this reaction and obtained repr6ducible results.…”

Section: Fig 1 Biogenetic Isomerizationmentioning

confidence: 99%

Syntheses of (highly reactive) functionalized isoprene building blocks and their application to di- and poly-isoprenoid syntheses

Huisman¹

1977

Pure and Applied Chemistry

View full text Add to dashboard Cite

-A convenient conversion of isoprene into highly reactive functionalized isoprene building blocks is described. Isoprene is readily co-oxidized with phenylmercaptan by molecular oxygen at roomtemperature to give a mixture of (mainly) 1-phenylsulfinyl-2-hydroxy-2-methylbutene-3 (obtained as two diastereoisomeric racemates) and 1-phenylsulfinyl-2-methyl-4-hydroxybutene-2 [obtained as the (E+Z)-isomers] in 96% conversion based on phenylmercaptan. Applications to the syntheses of various isoprenoids are outlined. Finally a new approach to the synthesis of vitamin E is given. Special attention is drawn to 2R, 4'R, 8'R-a-tocopherol-which, in all probabili ty -is one of nature' s best oxygi:m transfer agents.A possible "overall" scheme of the biochemical pathway of this (for human health indispensable) oxygen-transferring .. system is indicated. Evidence is given that it is one of the (main) causes of the epidemical coeurring heart and vascular diseases~ as well the increasing occurrence of cancer may be due to a lasting deficiency of this indispensable human health factor.

show abstract

The Reaction of Isoprene with t-Butyl Hypochlorite in Hydroxylic Solvents

Cited by 45 publications

References 0 publications

New cytokinin metabolites in IPT transgenic Arabidopsis thaliana plants

New cytokinin metabolites in IPT transgenic Arabidopsis thaliana plants

New Retinoid Analogs from δ-Pyronene, a Natural Synthon

Syntheses of (highly reactive) functionalized isoprene building blocks and their application to di- and poly-isoprenoid syntheses

Contact Info

Product

Resources

About