- RAS INHIBITORS
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The disclosure features macrocyclic compounds, and pharmaceutical compositions and protein complexes thereof, capable of inhibiting Ras proteins, and their uses in the treatment of cancers.
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Paragraph 0957; 0958
(2021/05/07)
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- Regioselective, Photocatalytic α-Functionalization of Amines
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Photocatalytic α-functionalization of amines provides a mild and atom-economical means to synthesize α-branched amines. Prior examples featured symmetrical or electronically biased substrates. Here we report a controllable α-functionalization of amines in which regioselectivity can be tuned with minor changes to the reaction conditions.
- Leng, Lingying,Fu, Yue,Liu, Peng,Ready, Joseph M.
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supporting information
p. 11972 - 11977
(2020/08/06)
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- Palladium-Catalyzed Diastereoselective Synthesis of 3-Arylbutanoic Acid Derivatives
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The first palladium-catalyzed diastereoselective conjugate addition of arylboronic acids to chiral imides is reported. The catalytic system employing 4-tert-butyloxazolidin-2-one as the chiral auxiliary in a mixed solvent system of MeOH/H2O (1:3) under an air atmosphere provides the optically active 3-arylbutanoic acid derivatives in excellent yields with high diastereoselectivity.
- Zhi, Wubin,Li, Jingya,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie
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p. 12286 - 12293
(2017/12/08)
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- THIOPHEN-2-CARBOXYLIC ACID DERIVATIVES USEFUL AS INHIBITORS OF FLAVIVIRIDAE VIRUSES
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Provided are compounds of Formula I: and pharmaceutically acceptable salts and esters thereof. The compounds, compositions, and methods provided are useful for the treatment of Flaviviridae virus infections (e.g. hepatitis C infections), particularly drug
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Page/Page column 31; 32
(2013/03/26)
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- Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: Synthesis of chiral fluorinated amino acids
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A novel conjugate hydrofluoroalkylation of α,β-unsaturated acyl-oxazolidinones is described. Using this method, enantiomerically pure β-trifluoromethylated amino acids were prepared. Trifluorovaline and trifluoroisoleucine were incorporated into peptides and found to show extremely low α-helix propensities.
- Erdbrink, Holger,Peuser, Ilona,Gerling, Ulla I. M.,Lentz, Dieter,Koksch, Beate,Czekelius, Constantin
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supporting information
p. 8583 - 8586
(2013/01/15)
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- Stereoselective synthesis of an alarm pheromone of Grematogaster ants using (4S)-4-benzyloxazolidinone as chiral auxiliary
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(S)-6-Methyl-3-octanone, a component of the alarm pheromone of Grematogaster ants, was synthesized through a key step of stereoselective Michael addition reaction using (4S)-4-benzyloxazolidinone as chiral auxiliary. The target product was obtained with a
- Zhou,Lu,Chen,Yang
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experimental part
p. 83 - 85
(2010/08/20)
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- Stereoselective synthesis of the sex pheromone of the yellow mealworm using (S)-4-benzyloxazolidinone as chiral auxiliary
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(R)-4-Methyl-1-nonanol, the sex pheromone of the yellow mealworn (Tenebrio molitor L.), was synthesized with high stereoselectivity using (S)-4-benzyloxazolidinone as chiral auxiliary. The stereoselective synthesis was achieved by asymmetric Michael addit
- Li,Lu,Yang,Chen
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experimental part
p. 440 - 443
(2010/10/02)
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- Doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure N-enoyl oxazolidin-2-ones: A mechanistic probe
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The doubly diastereoselective conjugate addition of the antipodes of lithium N-benzyl-N-(α-methylbenzyl)amide to a range of enantiopure N-enoyl oxazolidin-2-ones has been used as a mechanistic probe to determine that the reactive conformation is the anti-s-cis form. The β-amino carbonyl products resulting from these conjugate addition reactions are useful templates for further elaboration into an α,β,α-pseudotripeptide.
- Davies, Stephen G.,Fletcher, Ai M.,Hermann, Gesine J.,Poce, Giovanna,Roberts, Paul M.,Smith, Andrew D.,Sweet, Miles J.,Thomson, James E.
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experimental part
p. 1635 - 1648
(2010/10/18)
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- A concise diels-alder strategy for the asymmetric synthesis of (+)-albicanol, (+)-albicanyl acetate, (+)-dihydrodrimenin, and (-)-dihydroisodrimeninol
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A short, mild, highly diastereo-, regio-, and stereoselective Diels-Alder strategy has been developed for the asymmetric synthesis of (+)albicanol, (+)-albicanyl acetate, (+)-dihydrodrimenin, and (-)-dihydroisodrimeninol.
- Henderson, Jeff R.,Parvez, Masood,Keay, Brian A.
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supporting information; experimental part
p. 3178 - 3181
(2009/12/05)
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- Stereocontrolled total synthesis of (-)-kainic acid
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A stereocontrolled total synthesis of (-)-kainic acid is described. A fully functionalized trisubstituted pyrrolidine ring was constructed by ring-closing metathesis of an acrylate derivative followed by an intramolecular Michael addition of the resultant
- Sakaguchi, Hiroshi,Tokuyama, Hidetoshi,Fukuyama, Tohru
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p. 1635 - 1638
(2008/02/02)
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- Highly diastereoselective conjugate additions of monoorganocopper reagents to chiral imides
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Stereoselective conjugate additions to chiral N-enoyl amides employing various monoorganocuprate reagents, Li[RCuI], are described. The presence of TMSI in the addition of Li[RCuI] in THF provided the highest stereoselectivities. Reversed major diastereom
- Dambacher, Jesse,Anness, Robert,Pollock, Patrick,Bergdahl, Mikael
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p. 2097 - 2110
(2007/10/03)
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- 2-OXAZOLIDINONES AND THEIR USE AS INHIBITORS OF ANIMAL CELL MOTILITY AND GROWTH
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Cell motility and growth inhibitors, including compounds of the general structural formula (I), and use of the cell motility and cell growth inhibitors, and pharmaceutically acceptable salts, pro-drugs, and solvates thereof, as therapeutic agents, are disclosed.
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- Enantioselective synthesis of ceralure B1, ethyl cis-5-iodo-trans-2- methylcyclohexane-1-carboxylate
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Ethyl (1R, 2R, 5R)-5-iodo-2-methylcyclohexane-1-carboxylate is a potent attractant for the Mediterranean fruit fly. This compound was stereoselectively synthesized on a multigram scale in nine steps in 15% yield. Key steps of the synthesis involved an asymmetric Diels-Alder reaction, iodolactonization, stereoselective reduction of the carbonyl, and inversion of configuration with iodide. (C) 2000 Elsevier Science Ltd.
- Raw, Andre S.,Jang, Eric B.
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p. 3285 - 3290
(2007/10/03)
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- Stereoselective Conjugate Addition of Organoaluminum Chlorides to α,β-Unsaturated Carboxylic Acid Derivatives
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Organoaluminum chlorides react smoothly with α,β-unsaturated N-acyloxazolidinones providing chiral β-branched carboxylic acid derivatives.An unexpected contrast between the mode of reaction of dimethylaluminum chloride and that of the higher homologues is observed.While diethylaluminum chloride and its higher homologues react with the acceptors at low temperature via a polar pathway, dimethylaluminum chloride requires activation by UV-light or radical initiation under otherwise identical conditions.With bicyclic oxazolidinones derived from galactosamine a high stereoselection is accomplished in the formation of the branched carboxylic acid derivative.
- Rueck, Karola,Kunz, Horst
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p. 1018 - 1028
(2007/10/02)
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- Total synthesis of both (+)-compactin and (+)-mevinolin. A general strategy based on the use of a special titanium reagent for dicarbonyl coupling
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A strategy is described for stereocontrolled synthesis of hypocholesterolemic compounds, (+)-compactin and (+)-mevinolin, by an approach (Scheme II) based on 6, 7, 4-pentenal (9a), and (R)-3-methyl-4-pentenal (9b). The Evans asymmetric Diels-Alder technique was used (Scheme III) to prepare 13, which was converted into the cis ester 17. Chain extension, iodolactonization, and elimination of HI then gave optically pure 6. The homochiral epoxide 24, made (Scheme IV) from (S)-malic acid, was converted into 25 and then, by iodocarbonation, hydrolysis, and ketalization, into the iodo ketal 7. Evans asymmetric alkylation was used (Scheme V) to prepare 9b. Ozonolysis, ketalization, and reduction (LiAlH4) of 28 gave 31, which was transformed by Swern oxidation, Wittig methylenation, and acid hydrolysis into 9b. An optically pure intermediate (8), common to both syntheses, was assembled (Scheme VI) by alkylation of 6 with 7, reduction to a mixture of lactols, allylic oxidation, and decarbonylation. Aldol condensation (Scheme VII) of 8 with 4-pentenal, triethylsilylation, and ozonolysis gave the enone aldehydes 39, epimeric at C-1. A modified McMurry reaction requiring an excess of a reagent prepared from C8K and TiCl3 (2:1 molar ratio) in DME, produced the ethers 40, which were converted into (+)-compactin by appropriate modification of the oxygen functionality. The strategy is general and was applied with minor modifications (Scheme VIII) to the synthesis of (+)-mevinolin.
- Clive,Murthy,Wee,Prasad,Da Silva,Majewski,Anderson,Evans,Haugen,Heerze,Barrie
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p. 3018 - 3028
(2007/10/02)
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