- Synthesis of furanomycin derivatives by gold-catalyzed cycloisomerization of α-hydroxyallenes
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The novel furanomycin analogues 8 and 17 were synthesized as mixture of two diastereomers using the gold-catalyzed cycloisomerization of α-hydroxyallenes as the key step. Compared to the traditional use of stoichiometric amounts of silver salts, gold catalysis is much more efficient for the cyclization of highly functionalized substrates. Georg Thieme Verlag Stuttgart.
- Erdsack, Joerg,Krause, Norbert
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- Synthesis of new α-amino- acids containing the isoxazole moiety
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Methodology for preparing a series of novel α-amino-acids and their derivatives containing an isoxazole ring as a substituent is presented. The synthesis starts from a readily available L-serine derivative from which, depending on the synthetic strategy, it is possible to obtain isoxazol-3-yl or isoxazol-5-yl amino-acid precursors.
- Falorni, Massimo,Giacomelli, Giampaolo,Spanu, Emanuela
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Read Online
- Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid
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The synthesis of the four stereoisomers of a new 1,2,3-triazole analogue of rhizobitoxine from serine is described. The key step is a Huisgen 1,3-dipolar cycloaddition on an ethynylglycine synthon.
- Boibessot, Thibaut,Bénimèlis, David,Jean, Marion,Benfodda, Zohra,Meffre, Patrick
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supporting information
p. 2685 - 2688
(2016/11/30)
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- As cell necrosis inhibitors of the indole compounds (by machine translation)
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The invention relates to chemical formula (1) indole compounds, or its pharmaceutically acceptable salt or isomer, and in containing the same as the characteristic, as an active ingredient for the prevention or treatment of cell necrosis and its associated disease composition and method of manufacturing. (by machine translation)
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Paragraph 0223; 0224; 0242; 0243; 0244
(2016/10/09)
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- INDOLE COMPOUND AS INHIBITOR OF NECROSIS
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The present invention relates to an indole compound represented by formula (1), a pharmaceutically acceptable salt or isomer thereof, a composition for prevention or treatment of necrosis and necrosis-associated diseases, and a method for preparing the composition, the composition comprising the indole compound or the pharmaceutically acceptable salt or isomer thereof as an active ingredient.
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Paragraph 0191; 0192; 0193; 0203; 0204
(2016/08/17)
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- Gold-catalyzed oxycyclization of allenic carbamates: Expeditious synthesis of 1,3-oxazin-2-ones
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A combined experimental and computational study on regioselective gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out.
- Alcaide, Benito,Almendros, Pedro,Quiros, M. Teresa,Fernandez, Israel
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p. 818 - 826
(2013/06/05)
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- A macrocyclic approach to tetracycline natural products. Investigation of transannular alkylations and Michael additions
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A new approach to the tetracycline core structure is presented. The pivotal intermediate is identified as macrocycle III. The two interior bonds (C4a-C12a and C5a-C11a) are to be constructed through sequential transannular Michael additions (III-II) and compression-promoted transannular isoxazole alkylations from intermediate II.
- Wzorek, Joseph S.,Kn?pfel, Thomas F.,Sapountzis, Ioannis,Evans, David A.
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supporting information
p. 5840 - 5843
(2013/02/25)
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- Indium-mediated alkynylation of sugars: Synthesis of C-glycosyl compounds bearing a protected amino alcohol moiety
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The coupling of glycals with an alkynyl iodide bearing a protected amino alcohol moiety was achieved in the presence of metallic indium under Barbier conditions. It gave functionalized C-glycosyl compounds, precursors of C-glycosyl amino acids with α conf
- Ayed, Charfedinne,Palmier, Sara,Lubin-Germain, Nadge,Uziel, Jacques,Augé, Jacques
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scheme or table
p. 2566 - 2570
(2011/01/12)
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- Synthesis of alkynes and alkynyl iodides bearing a protected amino alcohol moiety as functionalized amino acids precursors
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Amino acid precursors in protected amino alcohol form are important synthons that can be used as building-blocks for the hemisynthesis of non-natural amino acids. Serine can be used as a common starting material for the synthesis of such compounds differe
- Ayed, Charfedinne,Picard, Julien,Lubin-Germain, Nadege,Uziel, Jacques,Auge, Jacques
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experimental part
p. 1921 - 1926
(2011/02/26)
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- A reasonably stereospecific multistep conversion of Boc-protected α-amino acids to Phth-protected β3-amino acids
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A method for the synthesis of β3-amino acids starting from α-amino acids is described. This conversion can be effected by an eight-step procedure which involves the transformation of the carboxylic group into an alkyne followed by a selenium-mediated conversion of the carbon-carbon triple bond to a Se-phenyl selenocarboxylate intermediate. The reactive Se-phenyl selenocarboxylate intermediates can be trapped with water, alcohols or the amine of an amino acid derivative to give β3-amino acids, β3-amino esters or mixed peptides, respectively. The whole transformations of the carboxylic group into an alkyne and of the alkyne group into β3-amino acids may not require purification of the intermediate products but a work-up and isolation procedure of crude materials.
- Temperini, Andrea,Capperucci, Antonella,Degl'Innocenti, Alessandro,Terlizzi, Raffaella,Tiecco, Marcello
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supporting information; experimental part
p. 4121 - 4124
(2010/08/20)
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- Cyclic peptide-polymer complexes and their self-assembly
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The efficient synthesis of novel chiral cyclic peptides cy-clo[NHCHX-CH=CHCH2CO(NHCH2-CH=CHCH2CO) 2] designed to develop hydrogen-bonding interactions with suitable polymers is described. Com-plexation of a carboxylic acid derivat-ized cyclic peptide 2 (X = CH2OCOCH2CH2CO2H) capable of self-assembling as "endless" tubes, with poly(vinyl alcohol) (PVA) led to a vast weak-interaction network, in which the cyclopeptide developed extensive hydrogen-bonding interactions with the hydroxyl groups of PVA through not only the carboxylic acid, but also its ester carbonyl and amide groups. In aqueous solution, the peptide/PVA complexes self-assemble into long-grain ricelike aggregates compatible with the stacking of cyclic peptides through intercycle hydrogen bonds. Upon casting on silicon wafer, the ani-sotropic aggregates can coalesce to form filaments tens of micrometers long. The study demonstrates that complexing functionalized cyclic peptides with polymers through hydrogen bonding is a useful approach for using polymers to mediate the self-assembly and self-organization of cyclic peptides.
- Belanger, Dominique,Tong, Xia,Soumare, Sadia,Dory, Yves L.,Zhao, Yue
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experimental part
p. 4428 - 4436
(2009/12/07)
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- Total synthesis of (+)-asperazine
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The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is ex
- Govek, Steven P.,Overman, Larry E.
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p. 8499 - 8513
(2008/02/09)
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- Synthesis of "Garner" aldehyde-derived cyclopropylboronic esters
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The "Garner" aldehyde has been used as a common intermediate for the preparation of the corresponding alkyne 7 and the alkenylboronic esters 12-16 (24-80%). Diastereoselective cyclopropanation afforded cyclopropylboronic esters 17-20 (60-84%, dr 22:78 to 92:8), the configurations of which were determined by chemical correlation (cyclopropanols 22), X-ray structural analysis (of 21a), and characteristic NMR spectroscopic data. The protected amino alcohols 23-26 and amino acids 27 have been synthesised from the cyclopropylboronic esters 19 by oxidation, Matteson homologation or Suzuki coupling. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
- Pietruszka, Joerg,Witt, Andreas,Frey, Wolfgang
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p. 3219 - 3229
(2007/10/03)
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- Practical one-step synthesis of ethynylglycine synthon from Garner's aldehyde
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A simple, efficient and practical synthesis of (R)-2,2-dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine (ethynylglycine synthon) is described. The method involves in situ formation of dimethyl 1-diazo-2-oxopropyl phosphonate from dimethyl 2-oxopropyl phosphonate and 4-acetamidobenzene sulfonyl azide and one-pot reaction on Garner's aldehyde. The reaction has been extended to other aminoaldehydes.
- Meffre, Patrick,Hermann, Sébastien,Durand, Philippe,Reginato, Gianna,Riu, Antonella
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p. 5159 - 5162
(2007/10/03)
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- A highly efficient and straightforward stereoselective synthesis of novel chiral α-acetylenic ketones
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A very efficient and straightforward synthesis of novel chiral α- acetylenic ketones of type 3 has been developed. Starting from commercially available l-(-)-serine 4, and through the Garner's aldehyde 5, ethynyloxazolidine 2 was formed in good overall yi
- Serrat, Xavier,Cabarrocas, Gemma,Rafel, Sara,Ventura, Montserrat,Linden, Anthony,Villalgordo, Jose M.
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p. 3417 - 3430
(2007/10/03)
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- Stereospecific synthesis of the amino acid, (S)-2-amino-(Z)- 3,5-hexadienoic acid
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The first synthesis of the amine acid, (S)-2-amino-(Z)-3,5- hexadienoic acid, a key component of the insecticidal dipeptide isolated from the Colorado Beetle, is reported. This was accomplished in 6 steps from Lajoie's protected serine aldehyde equivalent.
- Cameron, Stuart,Khambay, Bhupinder P.S.
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p. 1987 - 1990
(2007/10/03)
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- Synthesis of new chiral vinyl halides from L-serinal
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The synthesis of new chiral and functionalized vinyl halides from protected L-serinal is described.
- Branquet, Eric,Meffre, Patrick,Durand, Philippe,Le Goffic, Francois
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p. 613 - 622
(2007/10/03)
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- Synthetic Elaboration of the Side Chain of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynyloxazolidine: A New Regio- And Stereoselective Strategy to δ-Functionalized β-Amino Alcohols
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An investigation of the reactivity of ethynyloxazolidine 2 is presented. Functionalization at the acetylenic position has been found to occur very easily using the mild Sonogashira conditions. Addition of tributyltin cuprate 1 provided the corresponding stannylated (E)-ethenyloxazolidine 3, a new chiral building block which has been reacted with electrophiles under Pd catalysis. The reaction sequence occurred without racemization and showed an easy and mild procedure for the regio- and stereoselective synthesis of unsaturated amino alcohols.
- Reginato, Gianna,Mordini, Alessandro,Caracciolo, Massimo
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p. 6187 - 6192
(2007/10/03)
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- Elaboration of the side-chain of amino acid derivatives by palladium catalysed couplings
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The palladium-catalysed couplings of aryl halides and triflates with propargyl amino amides and the couplings of aryl and vinyl halides and triflates with an ethynyl oxazolidine are reported.
- Crisp, Geoffrey T.,Jiang, Yu-Lin,Pullman, Peter J.,De Savi, Chris
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p. 17489 - 17500
(2007/10/03)
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- Synthesis of optically active β,γ-alkynylglycine derivatives
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Full results on the first synthesis of optically active β,γ-alkynylglycine derivatives from naturally occurring L-serine are described. The methodology uses L-serinal as a key intermediate and allows great versatility in the introduction of N-protective groups and of alkyne substitution. The N-Boc protected β,γ-alkynylglycine derivatives described have ee greater than 90%.
- Meffre, Patrick,Gauzy, Laurence,Branquet, Eric,Durand, Philippe,Le Goffic, Francois
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p. 11215 - 11238
(2007/10/03)
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- En route to optically active ethynylglycine derivatives
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First results in the synthesis of chiral non racemic ethynylglycine derivatives from protected L-serinal are described.
- Meffre, Patrick,Gauzy, Laurence,Perdigues, Chantal,Desanges-Levecque, Florence,Branquet, Eric,Durand, Philippe,Le Goffic, Francois
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p. 877 - 880
(2007/10/02)
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- Stereoselective synthesis of (R)-(-)-2,2-dimethyl-3-t-butoxycarbonyl-4-ethynyloxazolidine: A chiral building block for the synthesis of a new class of substituted alkynes
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(R)-(-)-2,2-Dimethyl-3-t-butoxycarbonyl-4-ethynyl-oxazolidine (3a) has been prepared in good yield from chiral aminoaldehyde (4) through a two step procedure. Metalation of compound (3a) and subsequent reaction with electrophiles has been investigated lea
- Reginato, Gianna,Mordini, Alessandro,Degl'Innocenti, Alessandro,Caracciolo, Massimo
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p. 8275 - 8278
(2007/10/02)
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