An Efficient Stereocontrolled Synthesis of Di-and Triunsaturated Carbonyl Compounds

Mladenova, M.; Alami, Mouâd; Linstrumelle, G.

doi:10.1080/00397919608005217

Cited by 17 publications

(8 citation statements)

References 13 publications

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“…Its chemical structure was confirmed by 1 H- and 13 C-NMR, and IR spectra. The spectral data were consistent with those published in the literature [ 26 , 27 ].…”

Section: Resultssupporting

confidence: 89%

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Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity

et al. 2017

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The compounds produced by a living organism are most commonly as medicinal agents and starting materials for the preparation of new semi-synthetic derivatives. One of the largest groups of natural compounds consists of products containing a 1,4-benzoquinone subunit. This fragment occurs in three enediyne antibiotics, dynemicin A, deoxydynemicin A, and uncilamicin, which exhibit high biological activity. A series of alkoxy derivatives containing 1,4-naphthoquinone, 5,8-quinolinedione, and 2-methyl-5,8-quinolinedione moieties was synthesized. Moreover, the 1,4-benzoquinone subunit was contacted with an enediyne fragment. All obtained compounds were characterized by spectroscopy and spectrometry methods. The resulting alkane, alkene, alkyne and enediyne derivatives were tested as antitumor agents. They showed high cytotoxic activity depending on the type of 1,4-benzoquinone subunit and the employed tumor cell lines. The synthesized derivatives fulfill the Lipinski Rule of Five and have low permeability through the blood–brain barrier.

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“…Its chemical structure was confirmed by 1 H- and 13 C-NMR, and IR spectra. The spectral data were consistent with those published in the literature [ 26 , 27 ].…”

Section: Resultssupporting

confidence: 89%

“…6,7-dichloro-5,8-quinolinedione ( 2 ) and 6,7-dichloro-2-methyl-5,8-quinolinedione ( 3 ) were obtained according to methods described previously [ 36 ]. ( Z )-oct-4-ene-2,6-diyne-1,8-diol ( 22 ) was prepared according to the literature method [ 26 , 27 ].…”

Section: Methodsmentioning

confidence: 99%

Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity

et al. 2017

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“…CH 2 Cl 2 was distilled in the presence of P 2 O 5 . Chlorodienols14 1 , 5 and chloroenynols15 9 , 13 were prepared according to literature procedures.…”

Section: Methodsmentioning

confidence: 99%

An Iterative Procedure for the Synthesis of Conjugated ψ‐Chlorotrienoic and ‐tetraenoic Esters and Related Derivatives

et al. 2003

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An iterative stereoselective procedure for the synthesis of isomers of conjugated ψ‐chlorotrienoic esters and ψ‐chlorotetraenoic esters as well as related conjugated ψ‐chloropolyenynoic esters is described, using readily available conjugated chlorodienol and chloroenynol derivatives as starting materials. The two‐step sequence studied is based on repetition of a one‐pot conjugated allylic alcohol oxidation/Wittig reaction followed by a reduction step. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…Hence the corresponding E-isomer was prepared by Sonigashira coupling as before, followed by reduction with LiAlH 4 in Et 2 O at 0 °C giving (2E,4E)-5-chloropenta-2,4-dien-1-ol (3) in quantitative yield. 10 On attempted mesylation of either E,E or Z,E allylic alcohols, the only isolated product was the corresponding chloride 4 (64%) or 5 (61%), most probably formed by direct S N 2 displacement of the mesyloxy group by chloride ion.…”

Section: Scheme 1 Proposed Arene Retrosynthesismentioning

confidence: 99%

A Protocol for the Direct Conversion of Aldehydes into Arenes - Proof of Principle

Gayral¹,

Brown²

2007

Synlett

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An Efficient Stereocontrolled Synthesis of Di-and Triunsaturated Carbonyl Compounds

Cited by 17 publications

References 13 publications

Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity

Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity

An Iterative Procedure for the Synthesis of Conjugated ψ‐Chlorotrienoic and ‐tetraenoic Esters and Related Derivatives

A Protocol for the Direct Conversion of Aldehydes into Arenes - Proof of Principle

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An Efficient Stereocontrolled Synthesis of Di-and Triunsaturated Carbonyl Compounds

Cited by 17 publications

References 13 publications

Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity

Alkoxy and Enediyne Derivatives Containing 1,4-Benzoquinone Subunits—Synthesis and Antitumor Activity

An Iterative Procedure for the Synthesis of Conjugated ψ‐Chlorotrienoic and ‐tetraenoic Esters and Related Derivatives

A Protocol for the Direct Conversion of Aldehydes into Arenes - Proof of ­Principle

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A Protocol for the Direct Conversion of Aldehydes into Arenes - Proof of Principle