Acyloxyalkylidènephosphoranes—III

Hercouet, A.; Corre, M. Le

doi:10.1016/s0040-4020(01)92357-9

Cited by 65 publications

(31 citation statements)

References 18 publications

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“…59 ring closure by an intramolecular Wittig reaction [60][61][62] or o-(acyloxy)benzyl anions, 63 (c) condensation of activated methylene following Dieckmann reaction condtiions 64,65 or ketene intermediate involved cyclization, 66 (d) acid-catalyzed ring construction of a-aryloxycarbonyls 67 or (e) intramolecular Friedel-Cras reaction, 68 (f) photolytic cyclization of a-phenylketones, 69 and (g) gold(III)-catalyzed tandem reaction of O-arylhydroxylamines with 1,3-dicarbonyl substrates. 70 Moreover, a one-pot reaction for the transformation of allyl aryl ethers to 2-methylbenzofurans via sequential reaction involving Claisen rearrangement/oxidative cyclization has been reported.…”

Section: -39mentioning

confidence: 99%

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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Section: -39mentioning

confidence: 99%

Total synthesis of natural products containing benzofuran rings

et al. 2017

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“…Syntheses of the enynes 6 used a Wittig reaction [12,13], where the ylidium, prepared in situ using n-butyllithium, reacted rapidly with the intermediate aldehyde 4. The reaction proceeded stereospeci®cally and gave the desired product with yield of 33±35%.…”

Section: Thermotropic Liquid Crystals From Phenylpiperazine 25mentioning

confidence: 99%

Synthesis of Thermotropic Liquid Crystals Derived from Phenylpiperazine Containing an Enyne Unit

Gallardo

Maurmann

2002

Molecular Crystals and Liquid Crystals

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Thermotropic liquid crystals are of great technological importance. Much research is devoted to the development of stable compounds with transition temperatures close to room temperature. The interest of this work is the synthesis of thermotropic liquid crystal precursor units containing phenylpiperazine and=or phenylacetylenic units. Homologues of a Schi base series and an enyne series have been synthesized, allowing comparisons of their mesomorphic and thermodynamic properties. The Schi bases showed smectogenic behavior and the enynes a smectic dimorphism and=or a nematic phase. The synthetic methodology was ecient for the synthesis of the desired precursor, 4-[4 H -(prop-1-yn-3-al)phenyl]-piperazine-1-carboxylic acid ethyl ester.

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“…8 Another approach involves intramolecular Wittig cyclization on a phenolic ester followed by elimination of triphenylphosphine oxide to give the benzofuran. 9 Recently, polycyclic fused benzofurans were prepared by a TiCl 4 mediated Baylis-Hillman reaction of aromatic cyclic 1,2-diones with cycloalkenones followed by cyclization of the intermediates with methanesulfonic acid. 10 An interesting solid phase synthesis that involves the intramolecular alkylation of an aryloxy sulfonyl carbanion on an epoxide to generate an intermediate that loses formaldehyde and sulfinate to generate 3-arylbenzofuran ring systems has been reported.…”

mentioning

confidence: 99%

A new approach to fused furan ring systems and benzofurans: intramolecular cyclization reactions of unsaturated acyloxy sulfone derivatives

Liu¹,

Jacobs²,

Gopalan³

2011

Tetrahedron Letters

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Unsaturated acyloxy sulfones 3 undergo intramolecular cyclization upon deprotonation with LHMDS in THF. Dehydration and double bond isomerization of the products upon exposure to acid, gave the fused ring furans, 4, in good yields. This strategy could be readily adapted to 12 from the cyclization reactions of acyloxy sulfones 11 prepared from phenols. Finally, this approach could be successfully modified to access dihydropyrans and benzopyrans.

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Acyloxyalkylidènephosphoranes—III

Cited by 65 publications

References 18 publications

Total synthesis of natural products containing benzofuran rings

Total synthesis of natural products containing benzofuran rings

Synthesis of Thermotropic Liquid Crystals Derived from Phenylpiperazine Containing an Enyne Unit

A new approach to fused furan ring systems and benzofurans: intramolecular cyclization reactions of unsaturated acyloxy sulfone derivatives

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