- Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production
-
The piperazine heterocycle is broadly exploited in FDA-approved drugs and biologically active compounds, but its chemical diversity is usually limited to ring nitrogen substitutions, leaving the four carbon atoms underutilized. Using an efficient six-step synthesis, chiral amino acids were transformed into 3-substituted piperazine-2-acetic acid esters as diastereomeric mixtures whose cis and trans products (dr 0.56 a? 2.2:1, respectively) could be chromatographically separated. From five amino acids (both antipodes) was obtained a complete matrix of 20 monoprotected chiral 2,3-disubstituted piperazines, each as a single absolute stereoisomer, all but one in multigram quantities. In keeping with our overall purpose of constructing more Csp3-enriched compound libraries for drug discovery, these diverse and versatile piperazines can be functionalized on either nitrogen atom, allowing them to be used as scaffolds for parallel library synthesis and as intermediates for the production of novel piperazine compounds.
- Reddy Guduru, Shiva Krishna,Chamakuri, Srinivas,Raji, Idris O.,MacKenzie, Kevin R.,Santini, Conrad,Young, Damian W.
-
p. 11777 - 11793
(2018/09/27)
-
- Synthesis and biological activity of cyclolinopeptide A analogues modified with γ4-bis(homo-phenylalanine)
-
Cyclolinopeptide A (CLA), an immunosuppressive nonapeptide derived from linen seeds, was modified with S or R-γ4-bis(homo-phenylalanine) in positions 3 or 4, or both 3 and 4. These modifications changed the flexibility of new analogues and distribution of intramolecular hydrogen bonds. Analogues 11 c(Pro1-Pro2-Phe3-S-γ4-hhPhe4-Leu5-Ile6-Ile7-Leu8-Val9), 13 c(Pro1-Pro2-S-γ4-hhPhe3-R-γ4-hhPhe4-Leu5-Ile6-Ile7-Leu8-Val9) and 15 c(Pro1-Pro2-R-γ4-hhPhe3-Phe4-Leu5-Ile6-Ile7-Leu8-Val9) existed as a mixture of stable cis/trans isomers of Pro-Pro peptide bond. The comparison of the relative spatial orientations in crystal state of the two carbonyl groups, neighboring γ-amino acids, revealed conformational similarities to α-peptides. The addition of two -CH2- groups in γ-amino acids led to a more rigid conformation, although a more flexible one was expected. A significant difference in the relative orientation of the carbonyl groups was found for cyclic γ-peptides with a dominance of an antiparallel arrangement. As carbonyl groups may be engaged in the interactions with plausible receptors through hydrogen bonds, a similar biological activity of the modified peptides was expected. Our biological studies showed that certain cyclic, but not the corresponding linear peptides, lowered the viability of peripheral blood mononuclear cells (PBMC) at 100?μg/mL concentration. The proliferation of PBMC induced by phytohemagglutinin A (PHA) was strongly inhibited by cyclic peptides only, in a dose-dependant manner. On the other hand, lipopolysaccharide (LPS)-induced tumor necrosis factor alpha (TNF-α) production in whole blood cell cultures was inhibited by both linear and cyclic peptides. Peptide 15 c(Pro1-Pro2-R-γ4-hhPhe3-Phe4-Leu5-Ile6-Ile7-Leu8-Val9) blocked the expression of caspase-3, inhibited the expression of caspases-8 and -9 in 24?h culture of Jurkat cells, and caused DNA fragmentation in these cells, as an indicator of apoptosis. Thus, we revealed a new mechanism of immunosuppressive action of a nonapeptide.
- J?drzejczak, Karol,Hrynczyszyn, Pawe?,Szczesio, Ma?gorzata,Artym, Jolanta,Jastrz?bek, Tomasz,Koci?ba, Maja,G?ówka, Marek,Huben, Krzysztof,Kochanowska, Iwona,Zimecki, Micha?,Zabrocki, Janusz,Jankowski, Stefan,Kolesińska, Beata
-
p. 4265 - 4276
(2017/07/22)
-
- Efficient synthesis of functionalized olefins by Wittig reaction using Amberlite resin as a mild base
-
A convenient procedure for the synthesis of olefins by the reaction of stabilized, semistabilized, and nonstabilized phosphorous ylides with various aldehydes or ketone using Amberlite resin as a mild base is described. Our developed method offers facile and racemization-free synthesis of α,β-unsaturated amino esters and chiral allylic amine. The developed methodology offers mild reaction conditions, high efficiency, and facile isolation of the final products, a practical alternative to known procedures.
- Valkute, Tushar R.,Aratikatla, Eswar K.,Bhattacharya, Asish K.
-
p. 581 - 589
(2017/03/15)
-
- Non-classical Helices with cis Carbon–Carbon Double Bonds in the Backbone: Structural Features of α,γ-Hybrid Peptide Foldamers
-
The impact of geometrically constrained cis α,β-unsaturated γ-amino acids on the folding of α,γ-hybrid peptides was investigated. Structure analysis in single crystals and in solution revealed that the cis carbon–carbon double bonds can be accommodated into the 12-helix without deviation from the overall helical conformation. The helical structures are stabilized by 4→1 hydrogen bonding in a similar manner to the 12-helices of β-peptides and the 310helices of α-peptides. These results show that functional cis carbon–carbon double bonds can be accommodated into the backbone of helical peptides.
- Ganesh Kumar, Mothukuri,Thombare, Varsha J.,Katariya, Mona M.,Veeresh, Kuruva,Raja, K. Muruga Poopathi,Gopi, Hosahudya N.
-
supporting information
p. 7847 - 7851
(2016/07/07)
-
- Structural features and molecular aggregations of designed triple-stranded β-sheets in single crystals
-
Design, synthesis and single-crystal conformations of hybrid triple-stranded β-sheets composed of E-vinylogous residues are reported. Restricting conformational flexibility of β-strands through the insertion of carbon-carbon double bonds at facing positio
- Bandyopadhyay, Anupam,Misra, Rajkumar,Gopi, Hosahudya N.
-
supporting information
p. 4938 - 4941
(2016/04/10)
-
- Engineering polypeptide folding through trans double bonds: Transformation of miniature β-meanders to hybrid helices
-
Utilization of conjugated double bonds to engineer the novel folded miniature β-meander type structures, single step transformation of miniature β-meanders into ααγ4-hybrid peptide 10/12-helices using catalytic hydrogenation, their solution and single crystal conformations are reported.
- Ganesh Kumar, Mothukuri,Benke, Sushil N.,Poopathi Raja, K. Muruga,Gopi, Hosahudya N.
-
supporting information
p. 13397 - 13399
(2015/08/24)
-
- HBTU mediated 1-hydroxybenzotriazole (HOBt) conjugate addition: Synthesis and stereochemical analysis of β-benzotriazole N-oxide substituted γ-amino acids and hybrid peptides
-
HBTU is a standard coupling agent commonly used for the activation of free carboxylic acids during the solution and solid phase peptide synthesis. 1-Hydroxybenzotriazole (HOBt) plays a significant role in reducing the racemization during peptide synthesis
- Mali, Sachitanand M.,Ganesh Kumar, Mothukuri,Katariya, Mona M.,Gopi, Hosahudya N.
-
p. 8462 - 8472
(2015/01/09)
-
- Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain
-
Emergence and spread of multidrug resistant strains of Plasmodium falciparum has severely limited the antimalarial chemotherapeutic options. In order to overcome the obstacle, a set of new side-chain modified 4-aminoquinolines were synthesized and screened against chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of P. falciparum. The key feature of the designed molecules is the use of methylpiperazine linked α, β3- and γ-amino acids to generate novel side chain modified 4-aminoquinoline analogues. Among the evaluated compounds, 20c and 30 were found more potent than CQ against K1 and displayed a four-fold and a three-fold higher activity respectively, with a good selectivity index (SI = 5846 and 11,350). All synthesized compounds had resistance index between 1.06 and >14.13 as against 47.2 for chloroquine. Biophysical studies suggested that this series of compounds act on heme polymerization target.
- Sinha, Manish,Dola, Vasanth R.,Agarwal, Pooja,Srivastava, Kumkum,Haq, Wahajul,Puri, Sunil K.,Katti, Seturam B.
-
p. 3573 - 3586
(2014/07/07)
-
- A rapid entry to amino acid derived diverse 3,4-dihydropyrazines and dihydro[1,2,3]triazolo[1,5-a]pyrazines through 1,3-dipolar cycloaddition
-
An efficient, general and practical synthesis of diverse 3,4-dihydropyrazines, 6,7-dihydro-[1,2,3]triazolopyrazines and 7,8-dihydro-[1,2,3]triazolodiazepines through intramolecular 1,3-dipolar cycloaddition from amino acid derived common intermediates with high yields is described. Moreover, one-pot access to optically active 3-aryl substituted 6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazines in the palladium-copper co-catalytic system has also been achieved in this work. The easy substrate availability and operational simplicity make the process suitable for further exploration. This journal is the Partner Organisations 2014.
- Bera, Saurav,Panda, Gautam
-
p. 3976 - 3985
(2014/06/09)
-
- Self-assembly to function: Design, synthesis, and broad spectrum antimicrobial properties of short hybrid e -vinylogous lipopeptides
-
Nonribosomal E-vinylogous γ-amino acids are widely present in many peptide natural products and have been exploited as inhibitors for serine and cysteine proteases. Here, we are reporting the broad spectrum antimicrobial properties and self-assembled nanostructures of various hybrid lipopeptides composed of 1:1 alternating α- and E-vinylogous residues. Analysis of the results revealed that self-assembled nanostructures also play a significant role in the antimicrobial and hemolytic activities. In contrast to the α-peptide counterparts, vinylogous hybrid peptides displayed excellent antimicrobial properties against various bacterial and fungal strains. Peptides that adopted nanofiber structures displayed less hemolytic activity, while peptides that adopted nanoneedle structures displayed the highest hemolytic activity.
- Shankar, S. Shiva,Benke, Sushil N.,Nagendra, Narem,Srivastava, Prabhakar Lal,Thulasiram, Hirekodathakallu V.,Gopi, Hosahudya N.
-
supporting information
p. 8468 - 8474
(2013/12/04)
-
- Synthesis and stereochemical analysis of β-nitromethane substituted γ-amino acids and peptides
-
The high diastereoselectivity in the Michael addition of nitromethane to α,β-unsaturated γ-amino esters, crystal conformations of β-nitromethane substituted γ-amino acids and peptides are studied. Results suggest that the N-Boc protected amide NH, conformations of α,β-unsaturated γ-amino esters and alkyl side chains play a crucial role in dictating the high diastereoselectivity of nitromethane addition to E-vinylogous amino esters. Investigation of the crystal conformations of both α,β-unsaturated γ-amino esters and the Michael addition products suggests that an H-Cγ-CβC α eclipsed conformer of the unsaturated amino ester leads to the major (anti) product compared to that of an N-Cγ-C βCα eclipsed conformer. The major diastereomers were separated and subjected to the peptide synthesis. The single crystal analysis of the dipeptide containing β-nitromethane substituted γ-amino acids reveals a helical type of folded conformation with an isolated H-bond involving a nine-atom pseudocycle. The Royal Society of Chemistry 2013.
- Ganesh Kumar, Mothukuri,Mali, Sachitanand M.,Gopi, Hosahudya N.
-
p. 803 - 813
(2013/02/25)
-
- Hybrid peptides: Direct transformation of α/α, β-unsaturated γ-hybrid peptides to α/γ-hybrid peptide 12-helices
-
A smooth transformation of unusual planar structures of α/vinylogous hybrid peptides to ordered α/γ4-hybrid peptide 12-helices and the stereochemical preferences of vinylogous amino acid residues in single crystals are studied.
- Bandyopadhyay, Anupam,Gopi, Hosahudya N.
-
supporting information; experimental part
p. 2770 - 2773
(2012/07/28)
-
- α/γ4-Hybrid peptide helices: Synthesis, crystal conformations and analogy with the α-helix
-
Synthesis, crystal conformations of α/γ4-hybrid peptide helices containing proteinogenic amino acid side-chains, and the analogy with the α-helix are reported. Results suggest that α/ γ4-hybrid peptides adopted helical conformations
- Bandyopadhyay, Anupam,Jadhav, Sandip V.,Gopi, Hosahudya N.
-
supporting information; experimental part
p. 7170 - 7172
(2012/08/08)
-
- Synthesis of α, β-unsaturated γ-amino esters with unprecedented high (E)-stereoselectivity and their conformational analysis in peptides
-
Mild, efficient and racemization-free synthesis of N-protected α, β-unsaturated γ-amino esters with unprecedented high E- stereoselectivity is described. This method is found to be compatible with Boc-, Fmoc- and other side chain protecting groups. The crystal conformations of the vinylogous γ-amino esters in monomers and in homo- and mixed dipeptides are studied. Further, the vinylogous homo-dipeptide showed a β-sheet conformation, while mixed α- and α,β-unsaturated γ-hybrid dipeptide adapted an irregular structure in single crystals.
- Mali, Sachitanand M.,Bandyopadhyay, Anupam,Jadhav, Sandip V.,Kumar, Mothukuri Ganesh,Gopi, Hosahudya N.
-
p. 6566 - 6574
(2011/11/05)
-
- Novel CADD-based peptidyl vinyl ester derivatives as potential proteasome inhibitors
-
A series of peptidyl vinyl ester derivatives bearing three different P1 substitutions as potential proteasome inhibitors were studied. The target molecules were designed based on CADD (computer aided drug design) protocol and synthesized. Their activities
- Mou, Ke,Xu, Bo,Ma, Chao,Yang, Xiaoming,Zou, Xiaomin,Lue, Yang,Xu, Ping
-
p. 2198 - 2202
(2008/12/22)
-
- Design and synthesis of a novel class of furan-based molecules as potential 20S proteasome inhibitors
-
A novel class of furan-based compounds as potential 20S proteasome inhibitors have been designed and synthesized, among which nine compounds are peptide derivatives and six molecules are statine peptidomimetics. The C-terminal furanyl moiety was introduced to target molecules as furan-based amino acids. All the compounds were obtained steadily with moderate to high yield. Compound 12 was a selective moderate potent proteasome peptidomimetic inhibitor. It inhibited HepG2 and HL-60 proliferation effectively.
- Fu, Yiqiu,Xu, Bo,Zou, Xiaomin,Ma, Chao,Yang, Xiaoming,Mou, Ke,Fu, Gang,Lue, Yang,Xu, Ping
-
p. 1102 - 1106
(2007/10/03)
-
- Highly selective synthesis of enantiopure (S,E)-α,β-unsaturated γ-amino esters through a sequential reaction of ethyl dibromoacetate with α-amino aldehydes promoted by chromium dichloride
-
A sequential reaction of ethyl dibromoacetate with various enantiopure N,N-dibenzyl- or N-Boc-α-amino aldehydes (derived from natural α-amino acids), promoted by chromium dichloride, afforded optically active (S,E)-α,β-unsaturated γ-amino esters. The C=C
- Concellon, Jose M.,Mejica, Carmen
-
p. 5250 - 5255
(2008/03/30)
-
- IMIDAZOLIDINONE COMPOUNDS USEFUL AS BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
-
The present invention is directed to imidazolidinone compounds which are inhibitors of the beta- secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.
- -
-
Page/Page column 30
(2008/06/13)
-
- Highly stereoselective intramolecular SN2′ cyclization yielding chiral oxazolidin-2-ones: General route to α-hydroxy-β-amino acids
-
Intramolecular nucleophilic attack onto allylsulfonates promoted by silica gel acting as an acid catalyst provides expedient stereoselective access to 4,5-difunctionalized oxazolidin-2-ones. Precursors were prepared efficiently from enantiopure α-amino ac
- Seo, Woo Duck,Curtis-Long, Marcus J.,Kim, Jin Hyo,Park, Jong Keun,Park, Ki Min,Park, Ki Hun
-
p. 2289 - 2292
(2007/10/03)
-
- Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters
-
The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide α,β-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC50 > 100 μM), the ketomethylene isosteres and tripeptide α,β-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC50 = 11-39 μM). The Phe-Phe dipeptide inhibitors 18a-e are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor 18c with an inhibition constant of 0.52 μM is obtained by condensation of the Phe-Phe dipeptide α,β-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that 18c is a nontoxic anti-SARS agent with an EC50 value of 0.18 μM.
- Shie, Jiun-Jie,Fang, Jim-Min,Kuo, Tun-Hsun,Kuo, Chih-Jung,Liang, Po-Huang,Huang, Hung-Jyun,Wu, Yin-Ta,Jan, Jia-Tsrong,Cheng, Yih-Shyun E.,Wong, Chi-Huey
-
p. 5240 - 5252
(2007/10/03)
-
- Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels-Alder reaction
-
Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized
- Murray, William V.,Mishra, Pranab K.,Sun, Sengen,Maden, Amy
-
p. 7389 - 7392
(2007/10/03)
-
- Structure-based optimisation of 2-aminobenzylstatine derivatives: Potent and selective inhibitors of the chymotrypsin-like activity of the human 20S proteasome
-
We have identified 2-aminobenzylstatine derivatives that inhibit non-covalently the chymotrypsin-like activity of the human 20S proteasome. A structure-based optimisation approach has allowed us to improve the potency of this structural class of proteasome inhibitors from micromolar to nanomolar level. The new derivatives showed good selectivity against the trypsin-like and post-glutamyl-peptide hydrolytic activities of this enzyme.
- Furet, Pascal,Imbach, Patricia,Fuerst, Peter,Lang, Marc,Noorani, Maria,Zimmermann, Johann,Garcia-Echeverria, Carlos
-
p. 1331 - 1334
(2007/10/03)
-
- A new structural class of selective and non-covalent inhibitors of the chymotrypsin-like activity of the 20S proteasome
-
We describe the identification and in vitro characterization of a series of 2-aminobenzylstatine derivatives that inhibit non-covalently the chymotrypsin-like activity of the 20S proteasome. Our initial SAR data demonstrate that the 2-aminobenzylstatine core structure can effectively serve as the basis for designing potent, selective and non-covalent inhibitors of the chymotrypsin-like activity of the 20S proteasome.
- Garcia-Echeverria,Imbach,France,Fuerst,Lang,Noorani,Scholz,Zimmermann,Furet
-
p. 1317 - 1319
(2007/10/03)
-
- Diels-Alder Reactions of Amino Acid-Derived Trienes
-
Triene precursors (1a-e, 2a-k) were constructed for substrate-controlled asymmetric Diels-Alder reactions. Boc-L-phenylalanal and Boc-L-valinal were condensed with triethyl phosphonoacetate or 2-phosphonopropionate to generate the α,β-unsaturated esters as dienophiles. Removal of the Boc group to give free amines 4a-d, which after, or without N-benzylation, were treated with 3,5-hexadienoyl chloride to give 1a-e, or with 2,4-hexadienoyl chloride to afford 2a-f. The trienes 2g-i were prepared via reductive alkylation of amines 4a-i with 2,4-hexadienal. The secondary amide triene 1a failed to yield any Diels-Alder product when heated at 170°C. The tertiary amide trienes 1b-e produced in refluxing toluene the major cycloaddition products that were cis-fused and derived from the exo transition states. Trienes 2a-k underwent surprisingly facile Diels-Alder reactions to produce the major trans-fused isomers that were derived from the endo transition states. For trienes 2b-h and 2j,k, Diels-Alder reactions proceeded at room temperature. For the primary amide 2a, the Diels-Alder reaction proceeded smoothly in refluxing toluene. The tertiary amide triene 22 was constructed to have two electron-withdrawing ester substituents at the termini of the triene. The Diels-Alder reaction of 22 took place spontaneously at room temperature upon benzoylation of the secondary amine 21 and produced a single isomer derived from the endo transition state. 1,3-Allylic strain is discussed as an important factor in control of the diastereo-selectivity.
- Murray, William V.,Sun, Sengen,Turchi, Ignatius J.,Brown, Frank K.,Gauthier, A. Diane
-
p. 5930 - 5940
(2007/10/03)
-
- Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via π-allylpalladium complex catalyzed by Pd(0)
-
The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis and Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same π-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of β- amino-α-hydroxy acids 1 and γ-amino-β-hydroxy acids 2, conveniently protected as oxazoline.
- Lee, Kee-Young,Kim, Yong-Hyun,Park, Min-Sung,Oh, Chang-Young,Ham, Won-Hun
-
p. 9450 - 9458
(2007/10/03)
-
- Irreversible inhibitions of serine proteases by peptidyl allylic halide derivatives
-
Peptidyl 4-amino-5-phenyl-2-pentenyl bromide (7a, 9a, 10a) and chloride derivatives (7b, 9b, 10b) were found to be active-site directed irreversible inhibitors of α-chymotrypsin but did not show any irreversible inhibitory activity toward porcine pancreatic elastase. Copyright
- Ohba, Tsuyoshi,Ikeda, Eitatsu,Wakayama, Jun,Takei, Hisashi
-
p. 219 - 224
(2007/10/03)
-
- 2,4-DIAMINO-3-HYDROXYCARBOXYLIC ACID DERIVATIVES
-
The invention relates to compounds of formula I STR1 wherein the substituents have various significances. They can be prepared by conventional methods, e.g. coupling, substitution, deprotection or protection reactions.They possess interesting pharma
- -
-
-
- Stereoselective Syntheses of α-Hydroxy-γ-amino Acids: Possible γ-Turn Mimetics
-
Enantiomerically pure 4-amino-allyloxy-acetates, prepared from L-amino acids, undergo a stereoselective Wittig rearrangement with formation of the corresponding α-hydroxy-γ-amino acid esters having γ-turn conformational features.
- Reetz, Manfred T.,Griebenow, Nils,Goddard, Richard
-
p. 1605 - 1606
(2007/10/02)
-
- Inhibitors of HIV-1 proteinase containing 2-heterosubstituted 4-amino-3- hydroxy-5-phenylpentanoic acid: Synthesis, enzyme inhibition, and antiviral activity
-
A convenient procedure for the synthesis of 2-heterosubstituted statine derivatives as novel building blocks in HIV-protease inhibitors has been developed. The synthesis starts with protected L-phenylalaninols, which were converted to γ-amino α,β-unsatura
- Scholz,Billich,Charpiot,Ettmayer,Lehr,Rosenwirth,Schreiner,Gstach
-
p. 3079 - 3089
(2007/10/02)
-
- Syntheses and reactions of silyl carbamates. 2. A new mode of cyclic carbamate formation from tert-butyldimethylsilyl carbamate
-
Stereoselective construction of 1,2 and 1,3 amino hydroxyl systems was achieved by the intramolecular trapping of the N-tert-butyldimethylsilyloxycarbonyl species (silyl carbamate) activated by fluoride ion. The reaction of the silyl carbamate with 1,2-sy
- Sakaitani, Masahiro,Ohfune, Yasufumi
-
p. 1150 - 1158
(2007/10/02)
-
- A NEW MODE OF CYCLIC CARBAMATE FORMATION VIA tert.-BUTYLDIMETHYLSILYL CARBAMATE. STEREOSELECTIVE SYNTHESES OF STATINE AND ITS ANALOGUE
-
Stereoselective construction of 1,2- and 1,3-amino hydroxyl systems was carried out using SN2' (initiated by AgF or AgF-Pd(II)) cyclic carbamate formations from tert.-butyldimethyl silyl carbamates.This method was applied to the syntheses of st
- Sakaitani, Masahiro,Ohfune, Yasufumi
-
p. 3987 - 3990
(2007/10/02)
-