A comprehensive survey of stille-type Csp2-Csp2 single bond forming processes in the synthesis of retinoic acid and analogs

Domı́nguez, Beatriz; Iglesias, Beatriz; Lera, Ángel R. de

doi:10.1016/s0040-4020(99)00962-x

Cited by 50 publications

(31 citation statements)

References 117 publications

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“…In spite of the frequent presence of byproducts, these cross-coupling reactions have been applied with success to the synthesis of carotenoids. [35] According to the above results, it can be concluded that the Stille reaction, as shown here, is not a convenient method for the synthesis of polyene esters such as 8c, due to the generation of mixtures of compounds with very similar chromatographic properties on standard silica gel chromatography, although the reaction can be used for reaching the carbonyl-polyene conjugated compounds 8a and 8b.…”

Section: Introductionmentioning

confidence: 77%

Synthesis of Carboxyl‐Tethered Symmetric Conjugated Polyenes as Fluorescent Transmembrane Probes of Lipid Bilayers

2003

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The synthesis of a new series of fluorescent transmembrane probes in which two hydrophilic methyl ester or carboxyl groups are connected by a polymethylene chain, with four, five or six conjugated double bonds in a central position, is reported. The length of the linear structures was designed to match the width of typical lipid bilayers. These bolaamphiphilic compounds result, with overall yields higher than 80%, from an easy PdII‐catalyzed double cross‐coupling between terminal acetylene esters and conjugated 1,ψ‐dihalopolyenes, followed by selective triple bond partial reduction with activated zinc, and iodine isomerization to the all‐(E) isomer. An alternative approach, based on a Stille double cross‐coupling between the appropriate all‐(E)‐ψ‐halopolyenes and (E)‐bis(tributylstannyl)ethene, yielded mixtures that could not be resolved by standard chromatographic methods due to the presence of other simultaneous coupling reactions, which are also discussed in detail. Nevertheless, the Stille method can be of utility for the obtention of carbonyl‐polyene conjugated analogs. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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Section: Introductionmentioning

confidence: 77%

Synthesis of Carboxyl‐Tethered Symmetric Conjugated Polyenes as Fluorescent Transmembrane Probes of Lipid Bilayers

2003

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“…The Wittig or Horner-Wadsworth-Emmons reaction [29] and the Julia ole-fination [30] are the most often used double-bond-forming processes. Some pertinent examples are, for example, the stereocontrolled synthesis of 9-trans-9-fluororetinal, [32] the synthesis of retinoic acid and analogs, [33] the synthesis of symmetrical carotenoids, [34] a synthetic approach to the immunosuppressants SNF4435 C and SNF4435 D [35] and towards viridenomycin, [36] and the total synthesis of dermostatin A. With regards to this, the palladium-catalyzed coupling of organostannanes with organic electrophiles, developed by Stille, [31] owes its success, amongst other aspects, to the stability and low cross-reactivity of organotin compounds and the compatibility of the reaction conditions with many types of functional groups.…”

Section: Conjugated Dienes and The Stille Cross-couplingmentioning

confidence: 99%

Functionalized 1‐Alkoxy‐1,3‐dienes: Their Preparation and Applications in Synthetic Organic Chemistry

et al. 2006

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The reaction of various α,β‐unsaturated acetals with two equivalents of the Schlosser reagent LIC‐KOR [equimolar mixture of BuLi (LIC), and tBuOK (KOR)] gives 1‐metalated (1E)‐1‐alkoxy‐1,3‐dienes. These products can be transformed into trienic derivatives that are apt to participate in intramolecular Diels–Alder (IMDA) cycloaddition reactions, and can also be transformed into bifunctional (γ‐halo‐α‐carbonyl) reagents. Moreover, the metalated dienes can be readily functionalized with suitable electrophiles to afford products that have been found to be useful reagents for the Stille and Suzuki cross‐coupling reactions or arylated according to the conditions of the Heck process. Other significant syntheses of dienic and polyenic structures are reported along with some of their applications in organic synthesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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“…Among them, the synthetic application of fluorine-containing organostannanes in organic synthesis is still limited due to the limited methodology for their preparation [14]. The Stille crosscoupling reaction, which is a widely employed method for the carbon-carbon bond formation [15][16][17][18], has recently become a popular synthetic tool in organic synthesis, particularly for the synthesis of naturally occurring compounds [19][20][21][22][23][24][25][26][27]. Recently 1-fluorovinylstannanes [28], 1,2-difluorovinylstannanes [14,29], and trifluoromethylvinylstannanes [30] as coupling partners in Stille cross-coupling reaction have been reported.…”

Section: Introductionmentioning

confidence: 99%

Stille cross-coupling reaction of polyfluorovinylstannanes

Shen

Wang

2004

Journal of Fluorine Chemistry

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A comprehensive survey of stille-type Csp2-Csp2 single bond forming processes in the synthesis of retinoic acid and analogs

Cited by 50 publications

References 117 publications

Synthesis of Carboxyl‐Tethered Symmetric Conjugated Polyenes as Fluorescent Transmembrane Probes of Lipid Bilayers

Synthesis of Carboxyl‐Tethered Symmetric Conjugated Polyenes as Fluorescent Transmembrane Probes of Lipid Bilayers

Functionalized 1‐Alkoxy‐1,3‐dienes: Their Preparation and Applications in Synthetic Organic Chemistry

Stille cross-coupling reaction of polyfluorovinylstannanes

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