A short large scale synthesis of (±) sarkomycin esters

Amri, Hassen; Rambaud, M.; Villiéras, J.

doi:10.1016/s0040-4039(00)70702-7

Cited by 68 publications

(24 citation statements)

References 11 publications

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“…However, there have been several reports that this addition does occur to activated vinyl phosphorus systems. [9][10][11] Thus, in contrast to the expected acrylate 2, we obtained regioselectively the vinyl ester 5 in 78% yield (Scheme 1). (Figure 2).…”

Section: Resultsmentioning

confidence: 88%

Synthesis of pyrrol-[1,2-a]indole-1,8(5H)-diones as new synthones for developing novel tryciclic compounds of pharmaceutical interest

Sechi

Mura

Sannia³

et al. 2004

Arkivoc

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In the course of our work aimed at developing novel heterocycles of pharmaceutical interest, a new tricycle, the tetrahydropyrrolo[1,2-a]indole-1,8-dione, has been synthesized by an intramolecular Friedel-Crafts acylation, as a synthon suitable to be functionalized to give novel compounds with potential biological properties. Also, an unusual nucleophilic α-addition to methyl propiolate by 1,5,6,7-tetrahydro-4H-indol-4-one was observed and discussed.

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Section: Resultsmentioning

confidence: 88%

Synthesis of pyrrol-[1,2-a]indole-1,8(5H)-diones as new synthones for developing novel tryciclic compounds of pharmaceutical interest

Sechi

Mura

Sannia³

et al. 2004

Arkivoc

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“…Phosphonium ylides play an important role in the Wittig reaction and transition metal-catalyzed reactions in which the phosphines act as ligands, the nucleophilic tertiary phosphine adds to the triple bond of an electron-deficient alkyne first and finally eliminates from the reaction product after a series of transformations [1][2][3][4][5]. The tertiary phosphine plays the role of a catalyst [6,7].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 2-oxo-3-triphenylphosphonium-N-(phenyl)- maleinimidylid, C28H20NO3P

Fan¹,

Shen²

2008

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialTo a solution of 0.06 g (0.00014 mmol) triphenylphosphine, 0.173 g (1.0 mmol) N-phenylmaleimide and 0.201 g (1.5 mmol) 1-aminobenzotriazole in CH 2Cl2 (5 ml), 0.666 g (1.5 mmol) lead tetraacetate (LTA) with 5 ml CH 2Cl2 was added dropwise. After stirred at room temperature during 30 min, concentrated and then separated by flash chromatography on a silica gel column with petroleum ether / ethyl acetate as eluent. The title compound is one of the products (yield 2.4 %; m.p. 526 K). DiscussionPhosphonium ylides play an important role in the Wittig reaction and transition metal-catalyzed reactions in which the phosphines act as ligands, the nucleophilic tertiary phosphine adds to the triple bond of an electron-deficient alkyne first and finally eliminates from the reaction product after a series of transformations [1][2][3][4][5]. The tertiary phosphine plays the role of a catalyst [6,7]. In our recently experiments, the title compound was synthesized unexpectedly when we used triphenylphosphine as a catalyst to react with N-phenylmaleimide. In this reaction, the tertiary phosphine was not eliminated and acted as reactant. Similar to [8,9] the reaction mechanism keeps still unknown. The interplanar angles beween the maleimide ring and the three phenyl rings are 87.6(4)°, 68.1(7)°, 64.6(1)°. The dihedral angle between the maleimide ring and the N-phenyl group is 49.9(6)°.The bond distance of P-C27 2.738(2) Å, is a little shorter than normal distance of P-C bond (2.80 Å) [10].

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“…Consequently, we have tried to obtain compounds of type 2 via an esterification reaction of acid 1 through the use of some aliphatic alcohols in the presence of para-toluenesulfonic acid as catalyst in toluene at reflux. This coupling reaction afforded a new class of indene ring systems 2 bearing two different functional groups, which could be considered a new generation of Baylis-Hillman adducts 17 .…”

Section: Methodsmentioning

confidence: 99%

A facile approach towards the synthesis of functionalized indenol derivatives identified as potent anti-oxidant and anti-bacterial agents

et al. 2014

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An elegant one-pot synthesis of new indenols 2 was successfully carried out, starting from 1-hydroxy-1H-indene-2-carboxylic acid 1. Thus, esterification of acid 1 with aliphatic alcohols in toluene at reflux and a catalytic amount of para-toluenesulfonic acid afforded the corresponding alkyl esters 2 in moderate to good yields. This classical esterification process enables an efficient entry to a variety of new indenol-based molecular models 2, which could be adapted to a range of drug candidates. All the synthesized compounds 2a-e were subjected to the preliminary evaluation for their potential anti-oxidant and anti-bacterial activities. The assessment of radical scavenging capacity of the compounds 2a-e towards the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured and these compounds were found to scavenge DPPH free radical efficiently. Moreover, the in vitro antibacterial activity of derivatives 2a-e has been tested against a panel of pathogenic agents to show potent activity against all sensitive and resistant ones.

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A short large scale synthesis of (±) sarkomycin esters

Cited by 68 publications

References 11 publications

Synthesis of pyrrol-[1,2-a]indole-1,8(5H)-diones as new synthones for developing novel tryciclic compounds of pharmaceutical interest

Synthesis of pyrrol-[1,2-a]indole-1,8(5H)-diones as new synthones for developing novel tryciclic compounds of pharmaceutical interest

Crystal structure of 2-oxo-3-triphenylphosphonium-N-(phenyl)- maleinimidylid, C28H20NO3P

A facile approach towards the synthesis of functionalized indenol derivatives identified as potent anti-oxidant and anti-bacterial agents

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