- A concise synthesis of (-)-indolmycin and (-)-5-methoxyindolmycin
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Concise syntheses of (-)-indolmycin 1 and (-)-5-methoxyindolmycin 3 were developed based on a palladium-catalyzed reaction of (2S,3R)-2-acetoxy-3-methyl-5-trimethylsilyl-4-pentynoate 6 with an o-iodoaniline derivative 10 or 11, followed by reaction with g
- Sutou, Noriyuki,Kato, Keisuke,Akita, Hiroyuki
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- Total synthesis of ibogaine, epiibogaine and their analogues
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Efficient total synthesis of ibogaine, epiibogaine and their analogues has been described. An intramolecular reductive-Heck type cyclization was used for the construction of seven-membered indoloazepine ring to access iboga-skeleton. Larock's heteroannula
- Jana, Goutam Kumar,Sinha, Surajit
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- Modular counter-Fischer?indole synthesis through radical-enolate coupling
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A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.
- Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
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supporting information
p. 1096 - 1102
(2021/01/26)
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- Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes
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The cyclization order of the difunctional 1,2-diphenylethynes was precisely tuned under the catalysis of gold by changing the nitrogen substitution of the substrates, leading to the facile preparation of benzo[a]carbazole and indeno[1,2-c]quinoline derivatives. The mechanisms of these domino cyclizations were probed by control experiments, and an insight into the selectivity of the cyclization was gained by density functional theory (DFT) calculations. This research represents a unified and common method to access benzo[a]carbazoles and indeno[1,2-c]quinolines.
- Peng, Xiaoshi,Zhu, Lifeng,Hou, Yuqian,Pang, Yadong,Li, Yangming,Fu, Jiayue,Yang, Lu,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
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supporting information
p. 3402 - 3405
(2017/07/15)
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- Metal-free synthesis of fluorinated indoles enabled by oxidative dearomatization
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Nitrogen heterocycles are found in a majority of approved small-molecule pharmaceuticals, and the number of approved fluorinated drugs is increasing each decade. Therefore, new approaches for accessing fluorinated nitrogen heterocycles are of great significance. A novel, scalable, and metal-free method for accessing a wide range of fluorinated indoles is described. This oxidative-dearomatization-enabled approach assembles 2-trifluoromethyl NH-indole products from simple commercially available anilines with hexafluoroacetylacetone in the presence of an organic oxidant. The nature of the aniline N-capping group is critical for the success of this new reaction. Furthermore, the indole products contain a 3-trifluoroacetyl group, which can be exploited to access a plethora of useful functional groups.
- Vitaku, Edon,Smith, David T.,Njardarson, Jon T.
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supporting information
p. 2243 - 2247
(2016/02/18)
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- Synthesis of 4-Aryl-2-Quinolones via Copper-Catalyzed Hydroarylation of (o-Aminophenyl)propiolates with Arylboronates
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4-Aryl-2(1H)-quinolones were efficiently synthesized via copper-catalyzed hydroarylation of (o-aminophenyl)propiolates with arylboronic acid neopentyl glycol esters. The substrate propiolates were prepared from the corresponding silylalkynes with carbon d
- Murayama, Tsukasa,Shibuya, Masatoshi,Yamamoto, Yoshihiko
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supporting information
p. 166 - 171
(2016/02/14)
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- A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines
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The addition of InBr3 to the oxidative Sonogashira cross-coupling reaction of 2-ethynylaniline with (E)-trimethyl(3,3,3-trifluoroprop-1-enyl)silane led to a dramatic increase in the reactivity to afford the corresponding 1,3-enynes bearing a trifluoromethyl group on their terminal sp2 carbon. The subsequent cyclization of these 1,3-enynes under palladium catalysis provides access to the corresponding indoles bearing a 3,3,3-trifluoroprop-1-enyl group at their 2-position.
- Ikeda,Omote,Kusumoto,Komori,Tarui,Sato,Ando
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supporting information
p. 2127 - 2133
(2016/02/18)
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- Stereospecific approach to the synthesis of ring-A oxygenated sarpagine indole alkaloids. Total synthesis of the dimeric indole alkaloid P -(+)-dispegatrine and six other monomeric indole alkaloids
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The first regio- and stereocontrolled total synthesis of the bisphenolic, bisquaternary alkaloid (+)-dispegatrine (1) has been accomplished in an overall yield of 8.3% (12 reaction vessels) from 5-methoxy-d-tryptophan ethyl ester (17). A crucial late-stage thallium(III) mediated intermolecular oxidative dehydrodimerization was employed in the formation of the C9-C9′ biaryl axis in 1. The complete stereocontrol observed in this key biaryl coupling step is due to the asymmetric induction by the natural sarpagine configuration of the monomer lochnerine (6) and was confirmed by both the Suzuki and the oxidative dehydrodimerization model studies on the tetrahydro β-carboline (35). The axial chirality of the lochnerine dimer (40) and in turn dispegatrine (1) was established by X-ray crystallography and was determined to be P(S). Additionally, the first total synthesis of the monomeric indole alkaloids (+)-spegatrine (2), (+)-10-methoxyvellosimine (5), (+)-lochnerine (6), lochvinerine (7), (+)-sarpagine (8), and (+)-lochneram (11) were also achieved via the common pentacyclic intermediate 16.
- Edwankar, Chitra R.,Edwankar, Rahul V.,Namjoshi, Ojas A.,Liao, Xuebin,Cook, James M.
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p. 6471 - 6487
(2013/07/26)
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- Stereoselective synthesis of spirocyclic oxindoles based on a one-pot Ullmann coupling/Claisen rearrangement and its application to the synthesis of a hexahydropyrrolo[2,3-b]indole alkaloid
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An efficient and convenient approach to the synthesis of spirocyclic oxindoles from iodoindoles has been developed. The most striking feature of this approach is that the sequential intramolecular Ullmann coupling and Claisen rearrangement proceeds in a one-pot manner to afford 3-spiro-2-oxindoles in good yield with excellent diastereoselectivity. Application of this one-pot reaction to chiral non-racemic tertiary alcohol substrates resulted in complete chirality transfer to the spirocyclic quaternary carbon. Using this method, asymmetric total synthesis of (-)-debromoflustramine B was accomplished.
- Miyamoto, Hiroshi,Hirano, Tomohiro,Okawa, Yoichiro,Nakazaki, Atsuo,Kobayashi, Susumu
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supporting information
p. 9481 - 9493
(2013/10/08)
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- Consecutive gold(I)-catalyzed cyclization reactions of o -(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas: A one-pot synthesis of pyrimido[1,6- a ]indol-1(2 H)-ones and related systems
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Treatment of readily available o-(buta-1,3-diyn-1-yl-)-substituted N-aryl ureas such as 1 with the Au(I)-catalyst 11 affords, via a twofold cyclization process, the isomeric pyrimido[1,6-a]indol-1(2H)-one 3 in good yield.
- Sharp, Phillip P.,Banwell, Martin G.,Renner, Jens,Lohmann, Klaas,Willis, Anthony C.
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supporting information
p. 2616 - 2619
(2013/07/11)
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- Microwave-assisted synthesis of 3-substituted indoles via intramolecular arene-alkene coupling of o-iodoanilino enamines
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A generally applicable and high-yielding protocol for the synthesis of 3-substituted indole derivatives is described. Key features include microwave-assisted intramolecular arene-alkene coupling of o-iodoanilino enamines, and expedient synthesis of o-iodo
- Lee, Won-Il,Jung, Jong-Wha,Sim, Jaehoon,An, Hongchan,Suh, Young-Ger
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p. 7211 - 7219
(2013/08/23)
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- Synthesis of (±)-esermethole via an intramolecular carbamoylketene-alkene [2+2] cycloaddition
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A synthesis of (±)-esermethole (2), a synthetic precursor of physostigmine (1), has been accomplished by using an intramolecular carbamoylketene-alkene [2+2] cycloaddition followed by nitrone-mediated regioselective ring expansion for the construction of the basic carbon framework of 2 as the key steps.
- Ozawa, Tsukasa,Kanematsu, Makoto,Yokoe, Hiromasa,Yoshida, Masahiro,Shishido, Kozo
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p. 2927 - 2932
(2013/02/21)
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- Efficient synthesis of substituted quinolines through intramolecular addition of aryl anion to carbonyl carbon
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Substituted quinolines were synthesized in three steps from the Boc amides of substituted 2-iodoanilines and alkyl vinyl ketones. This method consists of (1) N-Michael addition of the Boc amide of 2-iodoaniline to alkyl vinyl ketone in the presence of Cs2CO3 in MeCN; (2) I-Mg exchange of the adduct with 3.5 equiv of i-PrMgCl·LiCl, and (3) acid-catalyzed reaction (excess AcCl in EtOH) of the resulting alcohol. Six examples are given with good yields.
- Kobayashi, Yuichi,Igarashi, Junji,Feng, Chao,Toshifumi,Tojo
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body text
p. 3742 - 3745
(2012/09/25)
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- Total synthesis of horsfiline: A palladium-catalyzed domino Heck-cyanation strategy
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A total synthesis of horsfiline has been accomplished featuring a key intramolecular palladium-catalyzed domino Heck-cyanation sequence for the formation of the 3,3′-disubstituted oxindole. Georg Thieme Verlag Stuttgart.
- Jaegli, Stephanie,Vors, Jean-Pierre,Neuville, Luc,Zhu, Jieping
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scheme or table
p. 2997 - 2999
(2010/03/03)
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- INDOLE DERIVATIVES AND DRUGS CONTAINING THE SAME
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An indole derivative represented by the following general formula (1) : wherein at least one of R1, R2, R3, and R4 represents an alkoxy group containing 1 to 20 carbon atoms, and other groups of the R1, R2, R3, and R4 represent hydrogen, an alkyl group containing 1 to 6 carbon atoms, acetyl group, or hydroxyl group; and either one of X and Y represents -(CH2)nOH wherein n is an integer of 0 to 30, and the other one of the X and Y represents hydrogen atom; or a salt thereof; and a drug and an agent for promoting differentiation of a stem cell containing such indole derivative or its salt as an effective component. The indole derivative (1) of the present invention has action of inducing differentiation of neural stem cell specifically into a neuron, and this indole derivative is useful as a prophylactic or therapeutic drug for brain dysfunction or neuropathy caused by loss or degeneration of the neuron.
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Page/Page column 20
(2010/02/11)
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- Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides
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A brief, efficient and economical synthesis of the spiropyrrolidinyloxindoles, horsfiline and coerulescine, has been achieved, starting from itaconic acid and, respectively, p-anisidine or o-iodoaniline. Tandem radical cyclisation of iodoaryl alkenyl azides is the key step in both syntheses.
- Lizos, Dimitrios E.,Murphy, John A.
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p. 117 - 122
(2007/10/03)
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- The synthesis of the kynurenamines K1 and K2, metabolites of melatonin
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An efficient synthesis of the kynurenamines K1 and K2, the major brain and antioxidant metabolites of melatonin 1 is described. Regioselective lithiation of tert-butyl(4-methoxyphenyl) carbamate and iodination provided the (2-iodoary
- Amiet, Gary,Hügel, Helmut M.,Nurlawis, Faizul
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p. 495 - 497
(2007/10/03)
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- A novel and economical route to (±)-horsfiline using an aryl iodoazide tandem radical cyclisation strategy
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(±)-Horsfiline has been synthesised using a tandem radical cyclisation as the key step.
- Lizos,Tripoli,Murphy
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p. 2732 - 2733
(2007/10/03)
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- General and facile synthesis of indoles with oxygen-bearing substituents at the benzene moiety
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Indoles with oxygen-bearing substituents such as a methoxy or (triisopropylsilyl)oxy group at all of the positions of the benzene moiety were synthesized by cyclization of tert-butyl methoxy(or (triisopropylsilyl)oxy)-2-((trimethylsilyl)ethynyl)phenyl)carbamates with potassium tert-butoxide in tert-butyl alcohol. The (ethynylphenyl)carbamates were synthesized by the palladium-catalyzed reaction of (trimethylsilyl)acetylene and the corresponding (iodophenyl)carbamates, which were selectively synthesized by directed lithiation of the phenylcarbamates and subsequent iodination.
- Kondo, Yoshinori,Kojima, Satoshi,Sakamoto, Takao
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p. 6507 - 6511
(2007/10/03)
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