C-Glycosylanthraquinone synthesis: total synthesis of vineomycinone B2 methyl ester

Tius, Marcus A.; Gómez-Galeno, Jorge; Gu, Xue; Zaidi, J. H.

doi:10.1021/ja00015a035

Cited by 122 publications

(59 citation statements)

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“…We feel that the wide range of substituted aromatic moieties that can be appended onto the carbohydrate nucleus, creating the unique carbon-carbon bond present in the C-aryl glycosides, makes this an attractive method for the preparation of this class of compounds. The preliminary investigations that have been reported from our laboratories (10, 11) and from other groups (15,17,(19)(20)(21) addressing the synthetic capabilities of the remaining en01 ether double bond in the C-aryl glucals are encouraging. Indeed, several stereoselective procedures have been developed, resulting in an important and general method for the preparation of C-aryl glycosides.…”

Section: Discussionmentioning

confidence: 71%

“…The mechanism that has been proposed for the Stille reaction (see Scheme 3) (40) involves a rapid oxidative addition of Pd (0) to the organic halide (here ArBr), followed by a slow transmetalation step with the organometallic partner to provide a diorgano-Pd(I1) species.10 We attributed the disappointing results that were observed in the attempted coupling reactions of 9~n a subsequent but related study, Tius et al noted that the rigorous exclusion of oxygen minimized the dimerization of a zinc glucal during palladium-mediated coupling reactions with aryl bromides (17). In addition, the oxidative addition of Pd(0) to a Six-X bonds has been reported (39).…”

Section: Tbdmso?' Otbdms T B D M S O~~ 33mentioning

confidence: 98%

“…[8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24]. Included in this list are aryl bromides containing electron-withdrawing and -donating substituents along with several highly substituted aromatics (see Table 1, entries [21][22][23][24].…”

Section: Stannyl-346-tri-o-(tert-butyldimethylsilyl)-o-glucal(li) Amentioning

confidence: 99%

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The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods

Friesen¹,

Loo²,

Sturino³

1994

Can. J. Chem.

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. Can. J. Chem. 72, 1262 (I 994).The C-aryl glucals 17-31 have been prepared by the palladium-catalyzed cross coupling of l-tributylstannyl-3,4,6-tri-0-(tert-butyldimethylsily1)-D-glcal (11) and aryl bromides. The major by-product in all of these reactions is the dimer 33, the product of homocoupling of 11. Alternatively, the C-aryl glucals 34-40 can be obtained from the palladium-catalyzed coupling of l-iodo-3,4,6-tri-0-(triisopropylsilyl)-~-glucal (16) and a variety of metalated aromatics, including ArZnC1, ArB(OH),, and ArB(OMe),. The advantages of the latter procedure include superior coupling yields under milder reaction conditions and the high yielding preparation of 16 directly from 3,4,6-tri-0-(triisopropylsily1)-D-glucal (12) by a metalation-iodination sequence.RICHARD W. FRIESEN, RICHARD W. LOO et CLAUDIO F. S m o . Can. J. Chem. 72, 1262Chem. 72, (1994.On a prCparC les C-aryl glucals 17-31 par un couplage croisC catalysC par le palladium du 1-tributylstannyl-3,4,6-tri-0-(tert-butyldimCthylsily1)-D-glucal (11) et des brornures d'aryle. Le sous-produit principal de toutes ces rkactions est le dimkre 33, le produit d'homocouplage du produit 11. On peut aussi obtenir les C-aryl glucals 34-40 par un couplage catalysC par le palladium du 1-iodo-3,4,6-tri-0-(triisopropylsilyl)-~-glucal (16) avec une variktC de produits aromatiques mCtallCs comportant le ArZnC1, le ArB(OH), et ArB(OMe),. Les avantages de la dernikre mCthode incluent des rendements supCrieurs de couplage dans des conditions plus douces et la pr~paration avec un rendement Clevk du composC 16 directement 2 partir du 3,4,6-tri-0-(triisopropylsily1)-D-glucal (12) par une sequence de metallation et d'iodation.[Traduit par la RCdaction]

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Section: Discussionmentioning

confidence: 71%

Section: Tbdmso?' Otbdms T B D M S O~~ 33mentioning

confidence: 98%

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The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods

Friesen¹,

Loo²,

Sturino³

1994

Can. J. Chem.

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“…This mixture was stirred at 0°C for 30 min and at room temperature for 4 h. Solvent evaporation followed by column chromatography of the residue on silica gel (CH 2 Cl 2 /MeOH, 20:1) produced 9 mg of (R)-fridamycin E methyl ester (20 %). R f (CH 2 : [5] [α] D 28 = -12 (c = 0.80, CHCl 3 )}. 1 …”

Section: Coupling Of Epoxide (S)-4a To Stannanementioning

confidence: 99%

A Chemoenzymatic, Enantioconvergent, Asymmetric Total Synthesis of(R)‐Fridamycin E

et al. 2005

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“…[12] Moreover, anthraquinones are well known to be the major active components in many traditional Chinese medicinal herbs. Due to the large number of different biological activities, [1] including purgative, antiinflammatory, astringent, [13] antioxidant, [14,15] antifungal, [16][17][18] antimicrobial, [19][20][21][22] antitumor, [23][24][25][26][27] larvicidal, [28] antiparasidal, [29,30] casein kinase II inhibitory, [31] antiviral, [32,33] and glucose-6-phosphate translocase (G6P-T1) inhibitory [34] properties, these compounds have become an attractive target for organic chemists. [35,36] In 1998, Arnold and co-workers [37] isolated a novel anthracene derivative 1 from the culture broth of Streptomyces sp.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Highly Functionalized Anthraquinones and Evaluation of Their Antitumor Activity

2007

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Highly functionalized anthraquinones which derive from the natural products mensacarcin, islandicin, and chrysophanol have been efficiently synthesized using a Diels–Alder reaction as key step. The introduction of the proposed pharmacophoric side chain unit has been achieved by an addition of an aryllithium species onto different aldehydes. Furthermore, the antitumor activity of these novel compounds has been studied by the in vitro growth inhibition of human lung carcinoma cells of line A549.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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C-Glycosylanthraquinone synthesis: total synthesis of vineomycinone B2 methyl ester

Cited by 122 publications

References 0 publications

The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods

The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods

A Chemoenzymatic, Enantioconvergent, Asymmetric Total Synthesis of(R)‐Fridamycin E

Synthesis of Highly Functionalized Anthraquinones and Evaluation of Their Antitumor Activity

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