- MACROCYCLIC COMPOUNDS
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Disclosed are macrocyclic compounds of formula (I) comprising a 2-carboxy indole ring. Such compounds, and their pharmaceutically acceptable salts, are useful as Mcl-1 (myeloid cell leukemia-1) inhibitors. The compounds may be used in treating a disease o
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Paragraph 0139
(2020/09/27)
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- PYRROLE COMPOUNDS
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Provided herein are compounds of Formula (I), or pharmaceutically acceptable salts thereof, pharmaceutical compositions that include a compound described herein (including pharmaceutically acceptable salts of a compound described herein) and methods of synthesizing the same. Also provided herein are methods of treating diseases and/or conditions with a compound of Formula (I), or a pharmaceutically acceptable salt thereof.
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Paragraph 0151
(2020/10/19)
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- MCL-1 INHIBITORS AND METHODS OF USE THEREOF
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Disclosed are Mcl-1 inhibitors, pharmaceutical compositions comprising the same and methods of using the same.
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Page/Page column 45; 48; 51
(2018/10/25)
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- MACROCYCLIC MCL1 INHIBITORS FOR TREATING CANCER
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Disclosed is a compound which is 17-chloro-5,13,14,22-tetramethyl-28-oxa-2,9-dithia-5,6,12,13,22-pentaazaheptacyclo[27.7.1.14,7.011,15.016,21.020,24.030,35]octatriaconta- 1(37),4(38),6,11,14,16,18,20,23,29,31,33,35-tridecaene-23-carboxylic acid (Formula I
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Page/Page column 37
(2017/11/15)
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- Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones
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A mimic of the Wacker process for C=O bond formation in terminal olefins can be initiated by a combination of the Pd(II) and hypervalent iodine reagent, Dess-Martin periodinane to generate methyl ketones. This operationally simple and scalable method offers Markovnikov selectivity, has good functional group compatibility, and is mild and high yielding.
- Chaudhari, Dipali A.,Fernandes, Rodney A.
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p. 2113 - 2121
(2016/03/15)
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- Synthesis of methyl ketones from terminal olefins using PdCl 2/CrO3 system mimicking the Wacker process
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An efficient synthesis of methyl ketones from terminal olefins using PdCl2/CrO3 system mimicking the Wacker process is developed. The method shows good functional groups compatibility, no aldehyde by-products and is operationally simple. CrO3 is the sole oxidant and replaces both Cu-salts and molecular oxygen, traditionally used in this process. The method holds potential for future applications in organic synthesis.
- Fernandes, Rodney A.,Bethi, Venkati
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p. 4760 - 4767
(2014/06/24)
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- Iron(III) sulfate as terminal oxidant in the synthesis of methyl ketones via wacker oxidation
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An efficient and environmentally benign method using Fe(III) sulfate as a terminal oxidant in the synthesis of methyl ketones from terminal olefins via the Wacker process is developed. The methodology offers high selectivity for a Markonikov product, shows good functional group compatibility, involves mild reaction conditions, and is operationally simple. Fe2(SO 4)3 is the sole terminal oxidant in this process. The method holds potential for future applications in organic synthesis.
- Fernandes, Rodney A.,Chaudhari, Dipali A.
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p. 5787 - 5793
(2014/07/08)
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- Palladium-catalyzed asymmetric quaternary stereocenter formation
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An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF 6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps. Copyright
- Gottumukkala, Aditya L.,Matcha, Kiran,Lutz, Martin,De Vries, Johannes G.,Minnaard, Adriaan J.
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supporting information; experimental part
p. 6907 - 6914
(2012/07/01)
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- Relative tendency of carbonyl compounds to form enamines
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Equilibria between carbonyl compounds and their enamines (from O-TBDPS-derived prolinol) have been examined by NMR spectroscopy in DMSO-d 6. By comparing the exchange reactions between pairs (enamine A + carbonyl B → carbonyl A + enamine B), a quite general scale of the tendency of carbonyl groups to form enamines has been established. Aldehydes quickly give enamines that are relatively more stable than those of ketones, but there are exceptions to this expected rule; for example, 1,3-dihydroxyacetone acetals or 3,5-dioxacyclohexanones (2-phenyl-1,3-dioxan-5-one and 2,2-dimethyl-1,3- dioxan-5-one) show a greater tendency to afford enamines than many α-substituted aldehydes.
- Sanchez, Dani,Bastida, David,Bures, Jordi,Isart, Carles,Pineda, Oriol,Vilarrasa, Jaume
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supporting information; experimental part
p. 536 - 539
(2012/03/26)
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- Total synthesis of iso- and bongkrekic acids: Natural antibiotics displaying potent antiapoptotic properties
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For over five decades, owing to their antiapoptotic activities, bongkrekic and isobongkrekic acids have generated interest from the scientific community. Here, we disclose full details of our investigation into the synthesis of isobongkrekic acid, which culminated in its first preparation and features various palladium-catalysed cross-couplings and Takai olefination reactions. Access to bongkrekic acid is also reported by this route. These syntheses involve the preparation and use of new general building blocks which could find wider applications. Iso-bong: A versatile first synthesis of isobongkrekic acid (IBA) has been developed. Key steps include three different palladium cross-couplings and an asymmetric homopropargylation. In-depth synthetic studies reveal the challenges faced in generating the right geometry of each diene.
- Francais, Antoine,Leyva-Perez, Antonio,Etxebarria-Jardi, Gorka,Pena, Javier,Ley, Steven V.
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experimental part
p. 329 - 343
(2011/03/21)
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- Total synthesis of the anti-apoptotic agents Iso- And bongkrekic acids
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(Figure presented) The first convergent total synthesis of isobongkrekic acid is reported involving three different stereospecific palladium cross-couplings for the formation of the diene units. Access to bongkrekic acid by this route is also demonstrated. These syntheses involve the formation of several potentially general building blocks.
- Francais, Antoine,Leyva, Antonio,Etxebarria-Jardi, Gorka,Ley, Steven V.
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supporting information; experimental part
p. 340 - 343
(2010/03/25)
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- Isolable gold(I) complexes having one low-coordinating ligand as catalysts for the selective hydration of substituted alkynes at room temperature without acidic promoters
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Hydration of a wide range of alkynes to the corresponding ketones has been afforded in high yields at room temperature by using gold(I)-phosphine complexes as catalyst, with no acidic cocatalysts required. Suitable substrates covering alkyl and aryl terminal alkynes, enynes, internal alkynes, and propargylic alcohols, including enantiopure forms, are cleanly transformed to the corresponding ketones in nearly quantitative yields. Acid-labile groups present in the substrates are preserved. The catalytic activity strongly depends on both the nature of the phosphine coordinated to the gold (I) center and the softness of the counteranion, the complex AuSPhOsNTf2 showing the better activity. A plausible mechanism for the hydration of alkynes through ketal intermediates is proposed on the basis of kinetic studies. The described catalytic system should provide an efficient alternative to mercury-based methodologies and be useful in synthetic programs.
- Leyva, Antonio,Corma, Avelino
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scheme or table
p. 2067 - 2074
(2009/08/07)
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- Asymmetric total synthesis of martinelline and martinellic acid
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Herein, we describe the first asymmetric total synthesis of (-)-martinelline ((-)-2) and the second total synthesis of (-)-martinellic acid ((-)-1) by employing a tandem Mukaiyama-Mannich reaction/aminal cyclization as the key step. The Royal Society of C
- Ikeda, Shuhei,Shibuya, Masatoshi,Iwabuchi, Yoshiharu
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p. 504 - 506
(2007/10/03)
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- Total synthesis of (±)-martinelline
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The squaric acid-catalyzed imino-Diels-Alder reaction of enamine 4 with the imine 5 provides the pyrroloquinolines 6 and 7, which were converted to the triamine 3 using regioselective reduction and a Wittig reaction as the key steps. Guanylation of 3 foll
- Xia, Chengfeng,Heng, Linshen,Ma, Dawei
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p. 9405 - 9409
(2007/10/03)
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- Synthesis and antitumor activity of a series of [2-substituted-4,5- bis(aminomethyl)-1,3-dioxolane]platinum(II) complexes
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The synthesis, physical properties, antitumor activity, structure-activity relationships, and nephrotoxicity of a series of [2-substituted-4,5- bis(aminomethyl)-1,3-dioxolane]platinum(II) complexes are described. The 42 platinum(II) complexes having a sev
- Kim,Kim,Gam,Cho,Kim,Tai,Kim,Hong -,Park
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p. 1471 - 1485
(2007/10/02)
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- A Concise and Enantioselective Approach to Cyclobutanones by Tandem Asymmetric Epoxidation and Enantiospecific Ring Expansion of Cyclopropylidene Alcohols. An Enantiocontrolled Synthesis of (+)- and (-)-α-Cuparenones
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A tandem Katsuki-Sharpless asymmetric epoxidation and enantiospecific ring expansion of 2-alkyl(or 2-aryl)-2-cyclopropylideneethanols (1a-i) afforded chiral 1-alkyl(or 1-aryl)-1-(hydroxymethyl)cyclobutanones (3a-i) in high yields and high enantiomeric excess.These compounds are potentially valuable synthons for the enantioselective creation of the quaternary carbons.Hence, this enabled us to accomplish a concise and enantioselective total synthesis of both (+)- and (-)-cuparenones (11).
- Nemoto, Hideo,Ishibashi, Hiroki,Nagamochi, Masatoshi,Fukumoto, Keiichiro
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p. 1707 - 1712
(2007/10/02)
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- THE REACTION OF O-SILYLATED α-KETOLS WITH TRIMETHYLSILYL CYANIDE
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The reactions of a series of O-silylated α-ketols with trimethylsilyl cyanide have been investigated.Formation of the expected O-trimethylsilyl cyanohydrins as major products has been shown to be accompanied by the hitherto unsuspected formation of a disi
- Still, Ian W. J.,Daoquan, Wang
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- Synthesis of 2-Butenolide and Tetronic Acid Analogues of Thiolactomycin
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A synthetic route to the three lactone analogues 2a-c of the interesting antibiotic thiolactomycin (1a) is described.The synthetic strategy used is flexible in that it allows in principle for variation in the nature of the substituents introduced at C-2,
- Still, Ian W. J.,Drewery, Michael J.
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p. 290 - 295
(2007/10/02)
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