Preparation of Some Methylated Gallic Acids

Shriner, R. L.; McCutchan, Philip

doi:10.1021/ja01382a033

Cited by 20 publications

(7 citation statements)

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“…26 It has been found that 2,5-disubstituted benzofurans are particularly active in enhancement of insulin sensitivity. 27 The benzofuran-fused benzocarbazol has been found to inhibit the growth of malignant cells and they also showed antibiotic properties (Fig. 3).…”

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Total synthesis of natural products containing benzofuran rings

et al. 2017

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Research on natural products containing benzofuran has remarkably increased during the past few decades.Newly isolated natural products with complex structures are being studied, characterized and screened for possible biological activities. Several of such compounds have exhibited various biological activities, thus their total syntheses have attracted much attention from synthetic organic chemists. In this review, we aim to highlight the origins, structures, biological potencies, and synthetic approaches of those natural products bearing at least one benzofuran in their complex structures. Furthermore, we especially focus on the step in which this key heterocycle is installed during the total synthesis of a natural product as the desired target.

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confidence: 99%

Total synthesis of natural products containing benzofuran rings

et al. 2017

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“…Soc., 55, 1204(1978. and homoegonol (3) and now report an adaptation of these procedures to a simple synthesis of (±)-machicendiol. By heating the readily available reactants, 5bromovanillin (4)2 3 and cuprous 3,4-methylenedioxyphenylacetylide (5)2 in pyridine solution, the required intermediate arylbenzofuranaldehyde (6) was obtained without difficulty.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of (.+-.)-machicendiol

Schneiders¹,

Stevenson²

1979

J. Org. Chem.

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“…In comparison, the preparation of uniformly labeled [4-13 C]benzene-1,2,4-triol would have required 7 reaction steps. For the preparation of side-chain labeled deacetylbolegrevilol (8*), 5-bromovanillin [21] (22) was subjected to Kabalka's variant of the Dakin reaction [22] (Scheme 7). The resulting bromo-methoxyhydroquinone 23 was deprotected [23] and subsequently treated with chloromethoxymethane to yield the tris-MOM ether 24.…”

Section: Syntheses Of Precursors Used For the Feeding Experimentsmentioning

confidence: 99%

“…To a mixture of THF (33 mL) and H 2 O (13 mL) were added with stirring 5-bromovanillin [21] (22, 2.31 g, 10 mmol) and sodium percarbonate (Na 2 CO 3 ϫ 1.5H 2 O 2 , 1.65 g, 10.5 mmol). The stirring was continued until the TLC indicated completion of the reaction (2.5 h).…”

Section: -Bromo-6-methoxybenzene-14-diol (23)mentioning

confidence: 99%

Studies on the Structure and Biosynthesis of Tridentoquinone and Related Meroterpenoids from the Mushroom Suillus tridentinus (Boletales)

et al. 2008

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Tridentoquinone (1), the main pigment of Suillus tridentinus, is accompanied by the known meroterpenoid bolegrevilol (3) and a dimer, tridentorubin (5). The absolute configuration of 1 was unambiguously established by a single‐crystal X‐ray analysis of the corresponding (–)‐camphanoate. The structure of 5 was elucidated by 2D NMR techniques including a 2D INADEQUATE experiment. Feeding experiments with [1‐13C]‐labeled 4‐hydroxybenzoic acid (6*) and 3,4‐dihydroxybenzoic acid (7*) proved the incorporation of these precursors into all three metabolites. Tridentoquinone (1) was monolabeled at C‐1 suggesting the formation of the ansa ring by oxidative cyclisation of 2‐geranylgeranyl‐6‐hydroxybenzoquinone (10). This was supported by the isolation of the expected intermediate, deoxytridentoquinone (11), from the mushroom extract. Tridentorubin (5) may be formed by addition of precursor 10 to tridentoquinone (1). This hypothesis is backed up by the in vitro formation of an analogous product 13 from 1 and 1,4‐benzoquinone. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Preparation of Some Methylated Gallic Acids

Cited by 20 publications

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Total synthesis of natural products containing benzofuran rings

Total synthesis of natural products containing benzofuran rings

Synthesis of (.+-.)-machicendiol

Studies on the Structure and Biosynthesis of Tridentoquinone and Related Meroterpenoids from the Mushroom Suillus tridentinus (Boletales)

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