<i>C</i>-Arylglycosides via a Benzannulation Mediated by Fischer Chromium Carbene Complexes

Pulley, Shon R.; Carey, James P.

doi:10.1021/jo980442h

Cited by 36 publications

(6 citation statements)

References 37 publications

(33 reference statements)

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“…The initial 3-isopropoxy-4-tributylstannylcyclobutene-1,2-dione 102 reacts with bromotetraphenylporphyrin and forms the corresponding 4-heteroaryl-3-isopropoxycyclobutene-1,2-dione 103. The catalyst was Pd 2 (dba) 3 During benzannelation of the dihydropyran ethynyl derivative 108 and the alkenylcarbene 109 followed by oxidation the quinone 110 was formed with a yield of 61% [105]. …”

Section: Construction Of the Quinone On The Basis Of A Heterocyclementioning

confidence: 99%

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

Batenko¹,

Karlivans²,

Valters³

2005

Chem Heterocycl Compd

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Methods for the synthesis of heteroaryl-substituted 1,4-benzo-and 1,4-naphthoquinones with a C-C bond between the heterocycle and quinone fragments are reviewed.Benzoquinones and their derivatives are widely used in organic synthesis as synthons and reagents [1,2]. They are used as electron-accepting components for the production of charge-transfer complexes and radicalion salts [3,4]. Derivatives of benzoquinones, isolated from natural sources, are subunits in many biological processes, such as electron transport, the photosynthesis of plants, the coagulation of blood, and cell respiration [1, 2, 5]. Reviews have been published on the synthesis of hydroxyquinones [6] and 1,4-benzoquinones condensed with heterocycles [7,8], but methods for the synthesis of heteroaryl derivatives of 1,4-benzoquinones and 1,4-naphthoquinones where the fragments of the heterocycle and the quinone are linked by a C-C bond have not so far been reviewed. Heteroaryl-substituted benzoquinones have demonstrated anticancer [9-11], antifungal, and antibacterial characteristics [11] and antidiabetic activity [12]. The present review is devoted to the analysis and classification of methods for the production of these compounds. Methods for the synthesis of heteroaryl derivatives of quinones can be divided into three groups: The formation of a C-C bond between the quinone and the heterocycle, construction of the heterocycle on the basis of the quinone, and construction of the quinone on the basis of the heterocycle.

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Section: Construction Of the Quinone On The Basis Of A Heterocyclementioning

confidence: 99%

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

Batenko¹,

Karlivans²,

Valters³

2005

Chem Heterocycl Compd

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“…17,18 The reaction of C-alkyne glycoside 2 with vinyl TMS carbene complex afforded C-arylglycoside 4 in 56% yield (Scheme 1). 17,18 The reaction of C-alkyne glycoside 2 with vinyl TMS carbene complex afforded C-arylglycoside 4 in 56% yield (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

“…We have successfully developed a new methodology for the synthesis of C-arylglycosides via a Dötz benzannulation reaction. 17,18 The reaction of C-alkyne glycoside 2 with vinyl TMS carbene complex afforded C-arylglycoside 4 in 56% yield (Scheme 1). The results showed that regioselective oxidation for the larger group of an unsymmetrical alkyne ortho to the phenolic hydroxyl group is consistent with the orientation of the naturally occurring C-arylglycosides such as medermycin.…”

Section: Introductionmentioning

confidence: 99%

Studies Towards the Synthesis of Medermycin via Dötz Benzannulation

Tang

Loeppky

et al. 2014

Chirality

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“…[22] We extended this methodology to organometallic O-and C-disaccharides in which both sugar moieties are linked by a metal vinylcarbene spacer, [23] as well as to organometallic C-glycosides formed by aldol condensation. [24] We now describe a synthetic route to hydroquinoid biphenyl disaccharides that are accessible by benzannulation reactions of an O-glycosidic α,β-unsaturated chromium carbene complex with an alkynyl C-glycoside.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Hydroquinoid C‐ and O‐Biphenyl Disaccharides by Chromium‐Templated Benzannulation Reactions

et al. 2003

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Organometallic monosaccharides 6−10 containing a chromium styrylcarbene skeleton have been synthesized in quantitative yield from O‐glycoside methylcarbene complexes 1−5 bearing diisopropylidene‐protected glucose, mannose, galactose, or fructose in a trans‐selective aldol condensation with benzaldehyde. These compounds undergo a chromium‐templated benzannulation upon reaction with ethynyl glucoside to give diastereoisomeric mixtures of Cr(CO)3 complexes. The differences in their thermodynamic stability was exploited in a diastereoselective synthesis of hydroquinoid biphenyl disaccharides 12−16 in 67−88% yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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C-Arylglycosides via a Benzannulation Mediated by Fischer Chromium Carbene Complexes

Cited by 36 publications

References 37 publications

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

Methods for the Synthesis of Heteroaryl-substituted 1,4-Benzo- and 1,4-Naphthoquinones. (Review)

Studies Towards the Synthesis of Medermycin via Dötz Benzannulation

Synthesis of Hydroquinoid C‐ and O‐Biphenyl Disaccharides by Chromium‐Templated Benzannulation Reactions

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