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Search for "formylation" in Full Text gives 59 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum
Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60
- , Germany) in N-methylpyrrolidone (NMP; VWR, Germany; c = 2 mol/L). Fmoc protecting groups were cleaved with 20% piperidine in DMF by using microwave irradiation as well. Formylation. The free N-terminus was formylated with 5 equiv para-nitrophenyl formate (pNPF; Sigma Aldrich, Germany) and 3 equiv N
Multicomponent synthesis of artificial nucleases and their RNase and DNase activity
Beilstein J. Org. Chem. 2011, 7, 1135–1140, doi:10.3762/bjoc.7.131
- or 12 carbon atoms by the standard formylation–dehydration protocol (Scheme 2). We found that these diisocyanides 3 participate successfully in the catalytic three-component reaction via a modified List procedure [25]. Diamides 4 with benzyl protective groups were synthesized in moderate to good
High chemoselectivity in the phenol synthesis
Beilstein J. Org. Chem. 2011, 7, 794–801, doi:10.3762/bjoc.7.90
- vinylcarbenoid F, the two competing reactions would be the formation of the phenol 10 and cyclopropanation to form 11. The synthesis of 8 was possible by a short route (Scheme 5). Starting from the commercially available 2-bromostyrene (12), a halogen–metal exchange and subsequent formylation according to a
Synthesis of 5-(6-hydroxy-7H-purine-8-ylthio)- 2-(N-hydroxyformamido)pentanoic acid
Beilstein J. Org. Chem. 2010, 6, 742–747, doi:10.3762/bjoc.6.93
- -formylation produced 12. Finally, debenzylation with boron tribromide afforded the hybrid molecule 13 as a slightly tan powder [9][10][11][12]. All compounds were fully characterized and their structures confirmed by 1H NMR and mass spectroscopy. The purity of the final product was determined by HPLC and
The efficient synthesis of dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene and cyclopenta[1,2-b:4,3-b′]bis(benzo[d]thiophen)-6-one
Beilstein J. Org. Chem. 2009, 5, No. 55, doi:10.3762/bjoc.5.55
- ] as starting material, dibenzo[d,d′]benzo[1,2-b:4,3-b′]dithiophene, a [5]heterohelicene, was synthesized efficiently in 60% yield via formylation and McMurry reaction. Cyclopenta[1,2-b:4,3-b′]bis(benzo[d]thiophen)-6-one, another interesting helical ketone, was also prepared in 79% yield via
- photolysis of RCH(SPh)2 (R = benzo[b]thiophene). However, a non-photochemical method for preparing 1 has, to the best of our knowledge, not been reported. In our work, with 3,3′-bis[benzo[b]thiophenyl] (3) [18] as starting material, 1 (see Figure 1) was synthesized efficiently via formylation and McMurry
- starting material, formylation and McMurry reaction were employed for preparing 1. The formylation step involves sequential deprotonation of 3 and treatment of the intermediate dilithiated species with N,N-dimethylformamide (DMF). Attempted generation of dilithiated 3 with either lithium diisopropylamide
Radical carbonylations using a continuous microflow system
Beilstein J. Org. Chem. 2009, 5, No. 34, doi:10.3762/bjoc.5.34
- pressurized carbon monoxide gas. Good to excellent yields of carbonylated products were obtained via radical formylation, carbonylative cyclization and three-component coupling reactions, using tributyltin hydride or TTMSS as a radical mediator. Keywords: continuous flow system; microreactor; radical
- CO and the liquid. Using the microflow system depicted by Figure 1, we carried out the radical formylation of 1-bromododecane (1) with CO in the presence of tributyltin hydride (bath temp. 80 °C) [21]. However, we encountered incomplete conversion of the starting bromide when we used AIBN (2,2
- carbonylation in a microflow system. The radical formylation of 1-bromododecane (1). 1-Bromododecane (1, 1 mmol, 249.5 mg), V-65 (0.1 mmol, 24.8 mg), Bu3SnH (1.2 mmol, 352.9 mg), and decane (59 mg) as an internal standard were dissolved in toluene (50 mL). The toluene solution was placed in a syringe (17 mL
Mitomycins syntheses: a recent update
Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33
A practical synthesis of the 13C/15N- labelled tripeptide N-formyl- Met-Leu-Phe, useful as a reference in solid- state NMR spectroscopy
Beilstein J. Org. Chem. 2008, 4, No. 35, doi:10.3762/bjoc.4.35
- Wolfgang Goethe University Frankfurt, Max-von-Laue-Str. 9, D-60438 Frankfurt am Main, Germany 10.3762/bjoc.4.35 Abstract A mild synthetic method for N-formyl-Met-Leu-Phe-OH (1) is described. After Fmoc solid phase peptide synthesis, on-bead formylation and HPLC purification, more than 30 mg of the fully
- 13C/15N-labelled tripeptide 1 could be isolated in a typical batch. This peptide can be easily crystallised and is therefore well suited as a standard sample for setting up solid-state NMR experiments. Keywords: Fmoc solid phase peptide synthesis; formylation; f-MLF; magic-angle spinning; Wang resin
- , reflux, 24–65 h) were required to couple the first Boc-protected amino acid to the solid support (chloromethyl resin) and long reaction times (18 h) were necessary to attach further building blocks to the growing peptide chain. The formylation of the N-terminus with formic acid/acetic anhydride was
Synthesis of the Benzo- fused Indolizidine Alkaloid Mimics
Beilstein J. Org. Chem. 2007, 3, No. 42, doi:10.1186/1860-5397-3-42
- . Palladium-catalyzed carboalkoxylation reaction of 12 gave the α-methoxycarbonyl dihydropyridone 13 in 82% yield. The addition and modification of functional groups on 8a were investigated (Scheme 4). The protection of the C-4 carbonyl of 8a as a ketal followed by Vilsmeier-Haack formylation [25] furnished
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