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1.
Wijdeven MA Botman PN Wijtmans R Schoemaker HE Rutjes FP Blaauw RH 《Organic letters》2005,7(18):4005-4007
The stereoselective total synthesis of the novel quinolizidine alkaloid (+)-epiquinamide is presented, starting from the amino acid l-allysine ethylene acetal. Key steps in the synthesis involved a highly diastereoselective N-acyliminium ion allylation and a ring-closing metathesis reaction to provide the bicyclic skeleton. [reaction: see text] 相似文献
2.
Floris P. J. T. Rutjes Henk Hiemstra Hendrik H. Mooiweer W. Nico Speckamp 《Tetrahedron letters》1988,29(52):6975-6978
Acid catalyzed cyclization of methoxymethyl substituted acyclic hydrazides 4 provides cyclic hydrazides 5 in moderate to good yields through the intermediacy of N,N′-di(methoxycarbonyl)hydrazinium intermediates. 相似文献
3.
[reaction: see text] Both unsaturated proline derivatives and optically active tryptophan analogues have been obtained via Pd-catalyzed cyclization of aniline-containing acetylenic amino acids. The side chain length of the cyclization precursor determines which one of the two possible products will be formed. 相似文献
4.
Vink MK Schortinghuis CA Luten J Van Maarseveen JH Schoemaker HE Hiemstra H Rutjes FP 《The Journal of organic chemistry》2002,67(22):7869-7871
A stereodivergent route toward both diastereomeric forms of functionalized 4-hydroxypiperidines has been successfully developed. This route involves biocatalytic generation of the enantiopure starting materials followed by functionalization via N-acyliminium ion-mediated CC-bond formation. 相似文献
5.
Kuijpers BH Groothuys S Keereweer AB Quaedflieg PJ Blaauw RH van Delft FL Rutjes FP 《Organic letters》2004,6(18):3123-3126
[structure: see text] An expedient, high-yielding synthesis of two types of triazole-linked glycopeptides is described. These novel and stable glycopeptide mimics were prepared via Cu(I)-catalyzed [3 + 2] cycloaddition of either azide-functionalized glycosides and acetylenic amino acids or acetylenic glycosides and azide-containing amino acids. 相似文献
6.
Veerman JJ Bon RS Hue BT Girones D Rutjes FP van Maarseveen JH Hiemstra H 《The Journal of organic chemistry》2003,68(11):4486-4494
Several 2-substituted and 2,5-disubstituted piperazine-3,6-diones were synthesized starting from readily available alpha-amino acids. After activation of a lactam carbonyl via introduction of a methoxycarbonyl group onto nitrogen, this carbonyl was selectively reduced. Treatment of the resulting urethane with protic acid generated the corresponding N-acyliminium ion, which was trapped by a nucleophilic C2-side chain to provide 2,6-bridged piperazine-3-ones. Several aromatic, heteroaromatic, and nonaromatic side chains were used as pi-nucleophiles. In addition, the effect of the presence of a C5-methyl group on the stereochemical outcome of the cyclization was examined. 相似文献
7.
Inside Cover: Quantitative Trace Analysis of Complex Mixtures Using SABRE Hyperpolarization (Angew. Chem. Int. Ed. 5/2015) 下载免费PDF全文
8.
Malik H Kohlen W Jamil M Rutjes FP Zwanenburg B 《Organic & biomolecular chemistry》2011,9(7):2286-2293
Strigolactones are signaling compounds in plants of increasing importance. In this paper the focus is on their activity as germinating agents for seeds of parasitic weeds. The syntheses of aromatic A-ring analogues of the germination stimulant orobanchol have been described. Starting substrate is the ABC unit of the stimulant GR24. Oxidation at the C-4 position gives a 4-oxo derivative which on subsequent reduction produces two C-4 epimeric alcohols, syn and anti in a ratio of 82 : 3. For practical access of the C-4 anti alcohol, the predominant syn epimer is inverted by a Mitsunobu procedure. The anti C-4 alcohol is then coupled with the D-ring in a one-pot two-step process involving a formylation and a reaction with bromobutenolide to give a mixture of the diastereomeric aromatic A-ring analogues of orobanchol. In contrast, the syn C-4 alcohol cannot be coupled directly with the D-ring. Protection of the C-4 syn OH is a prequisite. The best protecting function is the SEM group as deprotection after coupling with the D-ring can then readily be achieved. The structures of these new analogues have been ascertained by X-ray analyses. Both diastereomers of the C-4 syn as well as the C-4 anti orobanchol analogues have been tested as germination agents of seeds of Striga hermonthica and Orobanche ramosa. In addition, the acetates of both epimeric C-4 alcohols have been prepared and tested. Both diastereomers of the 4-oxo derivative have been prepared and bioassayed as well. The bioassays reveal that the diastereomers having the natural relative configuration are most active. The data also suggest that hydrogen bonding is not an important factor in the binding of the stimulant molecules in the receptor. 相似文献
9.
Kinderman SS Wekking MM van Maarseveen JH Schoemaker HE Hiemstra H Rutjes FP 《The Journal of organic chemistry》2005,70(14):5519-5527
[reaction: see text] Catalytic Sn(OTf)2-induced cyclization of linear, aryl-containing allylic N,O-acetals produced vinyl-substituted tetrahydroisoquinolines and tetrahydro-1H-beta-carbolines. The usefulness of the vinyl moiety in the resulting products was demonstrated via the synthesis of various key building blocks for alkaloid structures. The alpha-vinyl moiety was utilized in a [2,3] sigmatropic rearrangement, in ring-closing metathesis and a cross-metathesis-based synthesis of vincantril, an antianoxia agent, and a synthetic member of the vincamine type natural products. 相似文献
10.