A Chemoselective Synthesis of Functionalized 1,4-Alkadiynes (Skipped Diacetylenes)

Lapitskaya, M. A.; Vasiljeva, L. L.; Pivnitsky, K. K.

doi:10.1055/s-1993-25795

Cited by 56 publications

(25 citation statements)

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“…22,23 The alcohol 3 was converted to the corresponding bromide 4 in the presence of CBr 4 /PPh 3 . 24 Subsequent coupling of 4 with 1(trimethylsilyl)-1,4-pentadiyne in the presence of CuI, NaI, and K 2 CO 3 afforded tetrayne 5 in 71% yield.…”

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confidence: 99%

Total Synthesis and Bioactivity of 18(R)-Hydroxyeicosapentaenoic Acid

et al. 2011

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Resolvins are family of lipid mediators derived from omega-3 polyunsaturated fatty acids, which are generated during the resolution phase of acute inflammation. Resolvin E1 is biosynthesized from eicosapentaenoic acid via 18(R)-hydroxyeicosapentaenoic acid (18R-HEPE) in the Cox-2 and lipoxygenase mediated pathway and has proven to exhibit potent anti-inflammatory activity. We report herein the first total chemical synthesis of 18R-HEPE and demonstrate that this compound displays in vivo bioactivity by blocking neutrophil infiltration in a murine model of zymosan-induced peritonitis.

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confidence: 99%

Total Synthesis and Bioactivity of 18(R)-Hydroxyeicosapentaenoic Acid

et al. 2011

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“…Triyne 7 was achieved in good yield (71%) through a skipped alkyne synthesis by coupling propargyl bromide 8 with methyl 5-hexynoate 9. 17,18 A Z-stereoselective semireduction of triyne 7, was carried out via a modified Boland protocol using Zn(Cu/Ag) in presence of trimethylsilyl chloride (TMSCl) 19,20 at room temperature, to produce compound 6b in 65% yield. The modified Boland protocol, using Zn(Cu/Ag) in presence of TMSCl, proved to be important for this reaction 12,[20][21][22][23] (Scheme 1); the same reduction carried out with a Lindlar catalyst resulted in a complex mixture of products.…”

Section: Resultsmentioning

confidence: 99%

An efficient stereoselective synthesis of a sulfur-bridged analogue of bosseopentaenoic acid as a potential antioxidant agent

Mohamed¹,

Solum²

2017

Arkivoc

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An efficient approach to the stereoselective synthesis of a novel sulfur-bridged analogue of bosseopentaenoic acid (BPA) by employing the Z-selective modified Boland semi-reduction procedure as the key step is described. The free radical scavenging potential of the thiophene analogue of bosseopentaenoic acid is studied. The results showed that the thiophene ring led to increased antioxidant activity.

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“…2)). 13 Analysis of enantiomeric composition of diol 2. Pyridine (19 μL, 0.24 mmol) and BzCl (14 μL, 0.12 mmol) were sequentially added to a solution of diol 2 (10 mg, 0.06 mmol) in toluene (600 μL) at 0 °C.…”

Section: Methodsmentioning

confidence: 99%