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1.
Aucagne V Aversa MC Barattucci A Bonaccorsi P Giannetto P Rollin P Tatibouët A 《The Journal of organic chemistry》2002,67(20):6925-6930
A new method is described for building up anomeric glycosyl sulfoxides, via the formation of transient glycosulfenic acids and their addition to unsaturated acceptors. Thermolysis of alpha- and beta-3-[(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)sulfinyl]propanenitriles affords 1-glucosulfenic acids, which are reacted in situ with common substituted alkynes. The obtained (R(S),E)-2-[(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)sulfinyl]-2-butendioates are involved as enantiopure sulfinyl dienophiles in Diels-Alder reactions with 2,3-dimethyl-1,3-butadiene to evaluate the role that the sugar moiety plays in the steric control of the cycloaddition. This chemistry provides a direct synthetic strategy for the stereocontrolled connection between thioglycon and aglycon moieties, thus offering the basis for an easy elaboration of new molecules incorporating thiosugar residues. 相似文献
2.
Sünnemann HW Hofmeister A Magull J de Meijere A 《Chemistry (Weinheim an der Bergstrasse, Germany)》2006,12(32):8336-8344
A highly chemoselective sequence of Stille and Heck couplings on the heterocyclic bromoenol triflates 2 a-c with the bicycloalkenylstannanes cis-3 and trans-3 furnished the intermediate bromobutadienes 4 a-c in good yields ranging from 73-94 %. A modified Heck coupling protocol employing the palladacycle 8 and an additional bidentate ligand such as 1,4-bis(diphenylphosphinyl)butane allowed a significant reduction in catalyst loading while still obtaining the heterocyclic 1,3,5-hexatrienes 5 a-c in good yields (71-94 %). The unsymmetrically substituted 1,3,5-hexatrienes 5 a-c in solution underwent 6pi-electrocyclizations following an optimized microwave-heating protocol to yield the steroidal tetracycles cis-7 a-c and trans-7 b (59-69 %). Tetracycles cis-7 a-c are the products of a subsequent 1,5-hydrogen shift to the thermodynamically more stable, more highly substituted diene units. Removal of the tert-butyl groups provided the novel steroidal delta-amino acid 9 a and the delta-amino acid derivatives 9 b, c in good yields (76-86 %). 相似文献
3.
Ton That Thang Francois Winternitz Alain Lagrange Alain Olesker Gabor Lukacs 《Tetrahedron letters》1980,21(47):4495-4498
Appropriate precursors for the synthesis of D-vancosamine and L-evernitrose have been stereospecifically obtained from methyl 4,6-O-benzylidene-2-deoxy-α- and β-D-threo-hexopyranosid-3-ulose. 相似文献
4.
Marc-Antoine Bazin 《Tetrahedron letters》2007,48(25):4347-4351
An original strategy combining a Hunsdiecker-type bromodecarboxylation and a Suzuki cross-coupling reaction starting from various cinnamic acids has been developed in one-pot and under microwave heating to give trans-1,2-diarylethenes in few minutes. 相似文献
5.
W. Huber 《Tetrahedron letters》1985,26(2):181-184
The preparation of the radical anions of tetrabenzocyclooctatetraene (TBCOT) and fluorene (FLH) by photochemical methods leads to the observation of novel structures. 相似文献
6.
Diazo chemistry in the access to novel fatty acids linked to spiro-fused oxetane-pyrazolone scaffold
《Mendeleev Communications》2023,33(1):21-23
A novel free fatty acid mimetic based on the spirocyclic oxetane pyrazolone 1-oxa-6,7-diazaspiro[3.4]oct-7-en-5-one scaffold has been obtained in seven steps. The key stages are based upon the toolbox of diazo chemistry, including the F SAFE diazo transfer and RhII-catalyzed O–H insertion followed by base-triggered oxetane closing. 相似文献
7.
Novel symmetrically and unsymmetrically disubstituted 1-azaadamantanes were prepared as a single, chiral diastereomer via double microwave-assisted aza-Prins cyclization in one-pot or sequential reaction format. 相似文献
8.
The three isomers of pyridylpiperazines have been lithiated for the first time. The use of a superbase, an aminoalkoxide containing lithiating agent overcomes the chelating influence of the basic piperazine nitrogens, so that selective mono lithiation occurred alpha to pyridine nitrogen. This methodology offers a new access to diverse potent pharmacophores not easily prepared by other routes. 相似文献
9.
A novel, direct,and high-yielding stereoselective method for enantiopure 1-substituted tetrahydroisoquinolines (THIQ) is described. The successful approach, which creates the stereocenter during the formation of the THIQ nucleus is based on (i) formation of chiral 2,3-substituted perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol, (ii) diastereoselective intramolecular ring opening of the N,O-acetal moiety by an arylmetal generated from the substituent at the nitrogen atom in the perhydrobenzoxazine ring, and (iii) removal of the chiral auxiliary appendage. The starting perhydrobenzoxazines are easily prepared from (-)-8-aminomenthol and two different aldehydes, and the intramolecular opening is stereospecific, leading to a single stereoisomer. The method allows the preparation of a wide variety of enantiopure 1-substituted THIQ, with different substituents at C-1, by changing the nature of the starting aldehydes. 相似文献
10.
The synthesis of 2-methyl-3-(2-propenyl)pyrrole () and E- and Z-2-methyl-3-(1-propenyl)pyrroles () via the reaction of 3-butenyl methyl ketoxime () with acetylene in the KOH-DMSO system is reported. 相似文献
11.
The synthesis and chemical trapping of a highly pyramidalized pentacyclo[6.4.0.0(2,10).0(3,7).0(4,9)]dodec-8-ene containing ketal functions is reported. Its cross-coupling reaction with 3, 7-dimethyltricyclo[3.3.0.0(3,7)]oct-1(5)-ene followed by a [2 + 2] retrocycloaddition reaction gives a straightforward access to functionalized tetrasecododecahedradienes. 相似文献
12.
It is shown that lithium aggregates promoted the efficient metalation of phenylpyridines and stabilization of phenylpyridyllithium. The BuLi-LiDMAE superbase prevented dimerization or nucleophilic addition encountered with t-BuLi or n-BuLi. The reported selective pyridine ring lithiation of 2-, 3-, and 4-phenylpyridine alpha to nitrogen opens a straightforward access to their derivatives. 相似文献
13.
Stéphanie Gracia Cédric Marion Jullien Rey Florence Popowycz Stéphane Pellet-Rostaing Marc Lemaire 《Tetrahedron letters》2012,53(25):3165-3168
Horner-Wadsworth Emmons olefination followed by asymmetric hydrogenation allowed the first synthetic access to the chiral thiotryptophan with good enantiomeric excess. Oxazolidinone formation followed by a Pictet–Spengler condensation provided the benzothiophenic analog of Azatoxin. 相似文献
14.
Lohier JF Foucoin F Jaffrès PA Garcia JI Sopková-de Oliveira Santos J Perrio S Metzner P 《Organic letters》2008,10(6):1271-1274
A straightforward and high-yielding access to various [2.2]paracyclophanes possessing a sulfur-based functional group is reported, the key step being a SEAr reaction mediated by a sulfonium salt. The versatility of the methodology was exemplified by an original application in sulfenate salt chemistry, from which a remarkable chirality transfer was observed. 相似文献
15.
16.
《Tetrahedron letters》2004,45(10):2193-2196
Reduction with diphenylsilane and catalytic amounts of tris(triphenylphosphine)rhodium(I) carbonyl hydride resulted in an efficient, chemoselective method for the transformation of amino-acid-derived β-lactams into the corresponding azetidines, which after removal of the p-methoxybenzyl group, afforded a new family of conformationally restricted amino acids. Phe-derived compounds were obtained in enantiopure form by combining HPLC resolution of the β-lactam precursor and the above-mentioned procedure. 相似文献
17.
18.
John J. Parlow 《Journal of heterocyclic chemistry》1995,32(5):1413-1416
A novel formation of an oxepin, namely 9,10,11,12-tetrafluoro-5,6-dihydrobenzo[b]naphth[2,1-f]oxepin (5) , starting from pentafluoroacetophenone and 1-tetralone is described. Also, the same synthesis using 1-indanone affords a very different ring system namely 1,2,3,4-tetrafluoro-5,11b-dihydro-7H-benzo[c]fluoren-7-one (10) . Both synthesis undergo an intramolecular nucleophilic substitution of an ortho-fluorine. In one case, the oxygen displaces the fluorine to afford the oxepin 5 and the other a carbon is used as the nucleophile to give the polycyclic ring system 10 . 相似文献
19.
A straightforward semisynthesis of neohesperidose was performed in three-steps with 43% overall yield starting from naringin, the main flavonoid of grapefruit. In addition, the behaviour of two pairs of flavonoid 7-O-rhamnoglucosides (neohesperidosides naringin and rhoifolin; rutinosides hesperidin and diosmin) under same acetolysis conditions was compared. Results demonstrated the crucial influence of the oxidation state of the aglycone (flavanone or flavone), and of the nature of the disaccharidic moiety on the course of the reaction. 相似文献
20.
The combination of controlled polymerization techniques and "click" reactions form an efficient platform for the preparation of polymers in various architectures. In this critical review, an update of our 2007 review in Chem. Soc. Rev., we focus on the "click" reactions that have been used widely in the last four years to create new polymer architectures. Not only block copolymers and star-shaped polymers but also cyclic and dendritic macromolecules could be synthesized using these robust "click" reactions (205 references). 相似文献