A simple and practical synthesis of olivetol

Focella, Antonio; Teitel, S.; Brossi, Arnold

doi:10.1021/jo00441a036

Cited by 50 publications

(20 citation statements)

References 2 publications

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“…However, since the present study called for the incorporation of labelled C into the aromatic ring, it was decided to build the aromatic ring at a late stage of the synthesis, using diethyl malonate or [2-14 C]diethyl malonate at that point. This apparently straightforward route was used successfully for the synthesis of olivetol (C 5 : 0 ) by Focella et al (1977). However, with the twenty-one-C chain needed for our work, yields were found to be unreliable in the last two steps.…”

Section: Absorption Of Alkylresorcinols By Ratsmentioning

confidence: 94%

Absorption of dietary alkylresorcinols in ileal-cannulated pigs and rats

Ross

Shepherd

Knudsen³

et al. 2003

Br J Nutr

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Alkylresorcinols (AR) are amphiphilic 1,3-dihydroxy-5-alkyl phenolic lipids. AR in food are only found in the outer layers of wheat and rye grains, and in whole grains are present at concentrations of 500-1000 mg/g. In wheat and rye, there are five main homologues, differing in the length of the odd-numbered alkyl chain (from seventeen to twenty-five C atoms long). Because AR may be bioactive, and might serve as biomarkers for these cereals, their absorption was investigated in model experiments with pigs and rats. Pigs with a cannula in the terminal ileum were fed four diets containing rye fractions with different levels of AR and the ileal effluents were analysed. The ileal recovery of AR was found to vary between 21 and 40 %, with no major difference between different chain-length homologues. The absorption of AR by rats was investigated by feeding 14 C-labelled heneicosylresorcinol (C 21 : 0 ). Of the total activity, about 34 % was recovered in the urine, showing that the labelled AR was absorbed and metabolised by rats. AR were mostly cleared from rats by 60 h. It is concluded that AR are absorbed in the small intestine of single-stomached animals and excreted in metabolised form in the urine, and might contribute to the nutritional qualities of wholegrain wheat and rye diets.

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Section: Absorption Of Alkylresorcinols By Ratsmentioning

confidence: 94%

Absorption of dietary alkylresorcinols in ileal-cannulated pigs and rats

Ross

Shepherd

Knudsen³

et al. 2003

Br J Nutr

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“…However, for preparing the desired tetramethoxybiphenyls, we preferred to follow a route chosen by Lespugnol and Schmitt 1211 via intermediate 5-phenylcyclohexane-1,3-diones (cf. Scheme I), and already tested with the synthesis of hartwood constituents [22], olivetol [23], and diphenic acids related to the alkaloid protostephanine [24]. Elimination of undesired phenolic OH groups introduced during the aromatization of 1,3-diones, or by a Bueyer-Villiger oxidation (cJ Scheme 3) was envisaged to be accomplishable by catalytic hydrogenation of phenyl tetrazolyl ethers and investigated earlier [25] [26].…”

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confidence: 99%

Colchicine Models: Synthesis and Binding to Tubulin of Tertamethoxybiphenyls

Itoh¹,

Brossi²,

Hamel³

et al. 1988

Helvetica Chimica Acta

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Synthesis of tetramethoxybiphenyl21 was accomplished from 4-phenylcyclohexane-1,3-dione 13 by aromatization to biphenyl 19 and reductive removal of the phenolic OH group as phenyltetrazolyl ether. Tetramethoxybiphenyls 34 and 40 were obtained from 4-phenylcyclohexenone 26 via ester 27. The tetramethoxybiphenyls 21,34, and 40, and analogs 28, 29, and 31 were evaluated for antitubulin activity and as antimitotic agents with L1210 murine leukemia cells. Compounds 31 and 34 had significant effects on the in-vitro polymerization of tubulin. Compound 31 was the most cytotoxic of the six new biphenyls studied (ICs0 for cell growth, 0 . 6~) and caused the accumulation of cells in metaphase arrest.Introduction. -The antimitotic effect of colchicine and its inhibition of migration and phagocytosis of polymorphonuclear leukocytes are attributed to its binding to tubulin, which disorients the structural organization of microtubules [ 1-41. Data collected from studies of many colchicinoids (compounds chemically related to colchicine) in assays, measuring binding to tubulin in vitro an antitumor activity in vivo [4] [5], and inhibition of

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“…To show the synthetic utility of our developed method, we decided to apply diketone 10 e which could be used in the synthesis of tetrahydrocannabinol derivatives. For this purpose the reaction of cyclohexanedione 10 e 10 with trans ‐2‐hexenal ( 2 a ) was performed with 20 mol % of catalyst 3 b at room temperature for 48 h. After oxidation to the lactone, aromatization and decarboxylation with a 20 % sodium hydroxide solution, compound 15 was isolated in 45 % overall yield (over 4 steps) and an enantiomeric excess of 82 % (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…( R )‐5‐Methoxy‐7‐pentyl‐4‐propylchroman‐2‐one (15) : Compound 10 e 10 was subjected to the general procedure A (48 h at RT). The isolated product was subsequently oxidized with PCC according to the general procedure B.…”

Section: Methodsmentioning

confidence: 99%