157496-75-8Relevant articles and documents
A concise synthesis of (-)-indolmycin and (-)-5-methoxyindolmycin
Sutou, Noriyuki,Kato, Keisuke,Akita, Hiroyuki
, p. 1833 - 1838 (2008)
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
Total synthesis of ibogaine, epiibogaine and their analogues
Jana, Goutam Kumar,Sinha, Surajit
, p. 7155 - 7165 (2012)
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
Modular counter-Fischer?indole synthesis through radical-enolate coupling
Chung, Hyunho,Kim, Jeongyun,Gonzalez-Montiel, Gisela A.,Cheong, Paul Ha-Yeon,Lee, Hong Geun
supporting information, p. 1096 - 1102 (2021/01/26)
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.
Access to Benzo[a]carbazoles and Indeno[1,2-c]quinolines by a Gold(I)-Catalyzed Tunable Domino Cyclization of Difunctional 1,2-Diphenylethynes
Peng, Xiaoshi,Zhu, Lifeng,Hou, Yuqian,Pang, Yadong,Li, Yangming,Fu, Jiayue,Yang, Lu,Lin, Bin,Liu, Yongxiang,Cheng, Maosheng
supporting information, p. 3402 - 3405 (2017/07/15)
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.
Metal-free synthesis of fluorinated indoles enabled by oxidative dearomatization
Vitaku, Edon,Smith, David T.,Njardarson, Jon T.
supporting information, p. 2243 - 2247 (2016/02/18)
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.
Synthesis of 4-Aryl-2-Quinolones via Copper-Catalyzed Hydroarylation of (o-Aminophenyl)propiolates with Arylboronates
Murayama, Tsukasa,Shibuya, Masatoshi,Yamamoto, Yoshihiko
supporting information, p. 166 - 171 (2016/02/14)
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
A dramatic enhancing effect of InBr3 towards the oxidative Sonogashira cross-coupling reaction of 2-ethynylanilines
Ikeda,Omote,Kusumoto,Komori,Tarui,Sato,Ando
supporting information, p. 2127 - 2133 (2016/02/18)
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.
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
Edwankar, Chitra R.,Edwankar, Rahul V.,Namjoshi, Ojas A.,Liao, Xuebin,Cook, James M.
, p. 6471 - 6487 (2013/07/26)
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.
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
Miyamoto, Hiroshi,Hirano, Tomohiro,Okawa, Yoichiro,Nakazaki, Atsuo,Kobayashi, Susumu
supporting information, p. 9481 - 9493 (2013/10/08)
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.
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
Sharp, Phillip P.,Banwell, Martin G.,Renner, Jens,Lohmann, Klaas,Willis, Anthony C.
supporting information, p. 2616 - 2619 (2013/07/11)
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.
