- Total synthesis of indiacen A using a practical one-pot reaction: Promoted by a key waste product, and its utility in natural products synthesis
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Trialkylammonium salt, recognized as a waste product in the Heck reaction, was found to act as a key catalyst in the practical one-pot Heck-dehydration reaction. A concise synthesis of indiacen A was accomplished in 92% overall yield using a protecting-gr
- Wang, Lihua,Lei, Ting,Wang, Fusheng,Jiang, Shizhi,Yan, Guiyang
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Read Online
- Practical and efficient preparation of the chiral 4-bromotryptophan derivative by Rh-catalyzed hydrogenation
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An efficient three-step sequence has been developed for the preparation of a chiral 4-bromotryptophan derivative starting from the commercially available 4-bromoindole. Key to the synthesis was the generation of the chiral center via a Rh-catalyzed asymme
- Cai, Nengjian,Mi, Fen,Wu, Yanmei,Song, Hao,Liu, Xiao-Yu,Qin, Yong
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Read Online
- Pd(II)-Catalyzed Transient Directing Group-Assisted Regioselective Diverse C4-H Functionalizations of Indoles
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The development of a rational strategy for achieving site-selective C4-H halogenation of indoles is an appealing yet challenging task. Herein, we disclose a Pd(II)-catalyzed transient directing group (TDG)-assisted methodology for realizing C4 chlorination/bromination of indoles employing glycine as the TDG and NFSI as a bystanding oxidant. The use of inexpensive and commercially available CuX2as the halide source is the key highlight of this protocol. Furthermore, the TDG methodology was also extended to accessing C4 acetoxylated indoles employing acetic acid as the acetate source and 1-fluoro-2,4,6-trimethylpyridinium triflate as the oxidant.
- Dash, Om Prakash,Dey, Arnab,Pal, Kuntal,Singh, Anurag,Volla, Chandra M. R.
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p. 1941 - 1946
(2022/03/27)
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- Preparation method of non-natural L - tryptophan derivative
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The invention discloses a preparation method of a non-natural L - tryptophan derivative, which is sequentially subjected to formylation by adopting a cheap and easily available substituted indole compound as a raw material. Cyclization, ring opening, asym
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Paragraph 0086-0089
(2021/11/21)
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- Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids
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We report here a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids, which structurally feature a rigid cage scaffold, with L-tryptophan as the starting material. Two key bridged skeleton-forming reactions, namely tandem sequential oxidative cyclopropanol ring-opening cyclization and ketone α-allenylation, ensure concurrent assembly of the caged sarpagine scaffold and installation of requisite derivative handles. With a common caged intermediate as the branch point, by taking advantage of ketone and allene groups therein, total synthesis of five sarpagine alkaloids (affinisine, normacusine B, trinervine, Na-methyl-16-epipericyclivine, and vellosimine) with various substituents and three koumine alkaloids (koumine, koumimine, and N-demethylkoumine) with more complex cage scaffolds has been accomplished.
- He, Ling,Jiang, Yan,Qiao, Zhen,Qiu, Hanyue,Su, Xiaojiao,Tan, Qiuyuan,Yang, Jiaojiao,Yang, Zhao,Zhang, Min,Zhou, Wenqiang
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supporting information
p. 13105 - 13111
(2021/05/10)
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- Access to Polycyclic Indol(en)ines via Base-Catalyzed Intramolecular Dearomatizing 3-Alkenylation of Alkynyl Indoles
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Polycyclic indolines and indolenines were synthesized via base-catalyzed intramolecular dearomatizing 3-alkenylation reactions of alkynyl indoles 1 at room temperature. The base enhanced the nucleophilicity of the carbon at the 3-position of the indole moiety, facilitating an exclusive 5-exo-dig cyclization reaction with the alkyne to form spiroindolenines 2. The imine functionality of 2 could undergo in situ nucleophilic addition to form spiroindolines 3 when R was a carbamoyl group or reduction to form spiroindolines 4 when R was H.
- Liu, Bo,Lu, Lin,Yang, Yongjie,Yin, Biaolin,Zheng, Zuoliang
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supporting information
p. 2207 - 2212
(2021/07/06)
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- Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles
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Acyloxy-substituted α,β-unsaturated imines generated in situ from triazoles can act as aza-[4 C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system include operational simplicity, readily available substrates, construction of sterically demanding quaternary centers, and convenient derivatization using triflate. (Figure presented.).
- An, Yuehui,Chen, Yidian,Duan, Shengguo,Li, Chuan-Ying,Xu, Ze-Feng,Xue, Bing,Zhang, Wan
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supporting information
(2020/04/22)
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- Unusual Formation of Cyclopenta[ b]indoles from 3-Indolylmethanols and Alkynes
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Acid-promoted synthesis of cyclopenta[b]indole frameworks from 3-indolylmethanols and alkynes has been reported. The overall transformation represents a formal [3 + 2] annulation via rearrangement. This protocol showed good generality for the carbinol substrates as well as alkynes and allowed the generation of structurally diverse cyclopenta[b]indoles. Terminal alkynes, dialkyl-substituted internal alkynes, and alkynes with electron-deficient substituents were found to be not suitable for this transformation. Similarly, N-Ts and N-Boc groups were compatible with reaction conditions, whereas N-Ac and N-Tf failed to undergo this reaction. Isolation of vinyl chloride intermediate suggested the involvement of a vinylic carbocation intermediate. A mechanism has been proposed involving a ring-opening-ring-closing cascade followed by a 1,3-indole migration process via a spirocyclobutene intermediate.
- Gandhi, Soniya,Baire, Beeraiah
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p. 3904 - 3918
(2019/04/25)
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- Indiacens A synthetic method (by machine translation)
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The present invention provides a method of synthesizing Indiacens A, relates to the field of organic synthesis, comprising the following steps: (1) 4 - bromo indole - 3 - formaldehyde synthesis; (2) 4 - bromo indole - 3 - formaldehyde purification; (3) by 4 - bromo indole - 3 - formaldehyde synthetic Indiacens A, the invention has the cheap raw materials, the reaction mature, the synthesis step is short, advantage of high productive rate. (by machine translation)
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Paragraph 0029-0031; 0034; 0038
(2018/06/15)
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- Discovery of the cancer cell selective dual acting anti-cancer agent (Z)-2-(1H-indol-3-yl)-3-(isoquinolin-5-yl)acrylonitrile (A131)
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Selective targeting of cancer cells over normal cells is a key objective of targeted therapy. However few approaches achieve true mechanistic selectivity resulting in debilitating side effects and dose limitation. In this work we describe the discovery of A131 (4a), a new agent with an unprecedented dual mechanism of action targeting both mitosis and autophagy. Compound 4a was first identified in a phenotypic screen in which HeLa cells treated with 4a manifested mitotic arrest along with formation of multiple vesicles. Further investigations showed that 4a causes an increase in mitotic marker pH3 and autophagy marker LC3. Importantly 4a induces cell death in cancer cells while sparing normal cells which regrow after 4a is removed. Dual activities against pH3 and LC3 markers are required for cancer cell selectivity. An extensive SAR investigation confirmed 4a as the optimal dual inhibitor with potency against a panel of 30 cancer cell lines (average antiproliferative GI50 1.5 μM). In a mouse model of paclitaxel-resistant colon cancer, 4a showed 74% tumor growth inhibition when administered at a dose of 20 mg/kg IP twice a day.
- See, Cheng Shang,Kitagawa, Mayumi,Liao, Pei-Ju,Lee, Kyung Hee,Wong, Jasmine,Lee, Sang Hyun,Dymock, Brian W.
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p. 344 - 367
(2018/07/25)
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- Beta- tetrahydro-carboline antifungal drug and preparation method and application thereof
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The invention discloses a beta-tetrahydro-carboline antifungal compound and a pharmaceutically acceptable salt thereof. The structure of the compound is shown as the general formula I, wherein n is 1to 3; R1 is hydrogen or monosubstituted acetylene or polysubstituted acetylene in any optional position on the benzene ring, X is O or NH, R2 is substituted or unsubstituted aliphatic or aromatic ring; or X is NR3, R2 and R3 are individually lower alkyl and substituted or unsubstituted aliphatic or aromatic ring; or X is N, R2 and X composes substituted or unsubstituted heterocycloalkyl. The invention also discloses a preparation method of the compound and the application of the compound in preparation of antifungal drugs. The compound has the characteristic of well antifungal activity, the result of partial compound is better than that of the control drug fluconazole, and the compound can be utilized to prepare antifungal drugs. The experiment result also show that the combined usage of the partial compound and fluconazole has good synergistic effect to clinically isolated fluconazole-resistant candida albicans.
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Paragraph 0078; 0079; 0080; 0081; 0083; 0084; 0085
(2018/11/22)
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- Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)
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The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)
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Paragraph 0041-0044; 0106-0109
(2018/08/28)
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- ANTIBACTERIAL COMPOUNDS
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Novel compounds having antimicrobial activitiy, in particular against Pseudomonas aeruginosa, Burkholderia cepaciaand/or Clostridium difficile, and a pharmaceutical composition containing the novel compound.
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Page/Page column 31; 32
(2018/10/19)
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- IMIDAZOLYL-SUBSTITUTED INDOLE DERIVATIVES BINDING 5-HT7 SEROTONIN RECEPTOR AND PHARMACEUTICAL COMPOSITIONS THEREOF
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The invention relates to a new class of substituted indole derivatives that are able to activate 5-HT7 serotonin receptor. These compounds bind 5-HT7 serotonin receptor with high affinity and selectivity, while possessing favourable physicochemical properties. The compounds of the invention are the first described low-basicity 5-HT7 receptor agonists. The invention also relates to use of such compounds in the treatment or prevention of 5-HT7 receptor-related disorders, especially of the central nervous system. The invention also relates to the isotopically labelled compounds for use in the in vivo diagnostics or imaging of a 5-HT7 serotonin receptor.
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Page/Page column 15; 29; 30
(2018/02/28)
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- Total Syntheses of Pyroclavine, Festuclavine, Lysergol, and Isolysergol via a Catalytic Asymmetric Nitro-Michael Reaction
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A catalytic enantioselective construction of vicinal stereocenters is reported. The reaction takes advantage of thiourea-catalyzed intramolecular nitronate addition onto α,β-unsaturated ester to afford exceptional levels of enantioselectivity (up to 97 % ee) with moderate diastereoselectivity (up to 4:1). Using this method, a cross-conjugated ester was synthesized in few steps, from which a 6-endo-trig cyclisation led to the formation of all required functionalities for total syntheses of ergot alkaloids. The strategy not only offers first total syntheses of ergot alkaloids, festuclavine (1 c), and pyroclavine (1 e), and but also an efficient and general approach to other congeners such as, lysergol (1 b), and isolysergol (1 d).
- Bhunia, Subhajit,Chaudhuri, Saikat,Bisai, Alakesh
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supporting information
p. 11234 - 11238
(2017/08/26)
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- Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air
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An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.
- Wang, Qing-Dong,Zhou, Bin,Yang, Jin-Ming,Fang, Dong,Ren, Jiangmeng,Zeng, Bu-Bing
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supporting information
p. 2670 - 2674
(2017/10/06)
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- A Modular Formal Total Synthesis of (±)-Cycloclavine
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Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence. (Chemical Equation Presented).
- Netz, Natalie,Opatz, Till
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p. 1723 - 1730
(2016/03/01)
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- Organocatalytic enantioselective synthesis of C3 functionalized indole derivatives
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A highly enantioselective Michael addition reaction of indolylnitroalkenes with 1,3-dicarbonyl compounds has been developed to obtain enantiomerically enriched 3-(2-nitro-1-(1-tosyl-1H-indol-3-yl)ethyl)pentane-2,4-dione derivatives in up to 98% ee using BnCPN as an organocatalyst. The transition state structure has been predicted using DFT calculation.
- Kaur, Jasneet,Islam, Nasarul,Kumar, Akshay,Bhardwaj, Vimal K.,Chimni, Swapandeep Singh
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p. 8042 - 8049
(2016/11/22)
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- Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides
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A highly efficient N,N′-dioxide-NiII catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C-C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98 % yield with up to 91 % enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). A promising approach: Catalytic de-aromatic [3+2] cycloaddition of indoles with epoxides by C-C cleavage of oxiranes is accomplished by using a highly efficient N,N′-dioxide-NiII catalyst system. A range of chiral furo[3,4-b]indoles is obtained with high enantiomeric excesses and diastereomeric ratios.
- Chen, Weiliang,Xia, Yong,Lin, Lili,Yuan, Xiao,Guo, Songsong,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 15104 - 15107
(2015/11/02)
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- Cu-mediated oxidative dimerization of skatole to tryptanthrin, an indolo[2,1-b]quinazolone alkaloid
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A one-pot conversion of skatole to tryptanthrin, an indolo[2,1-b]quinazoline alkaloid, was achieved by Cu-mediated oxidation.
- Itoh, Tomoki,Abe, Takumi,Nakamura, Shuhei,Ishikura, Minoru
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p. 1423 - 1428
(2015/07/15)
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- Chiral anion phase transfer of aryldiazonium cations: An enantioselective synthesis of C3-diazenated pyrroloindolines
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Herein is reported the first asymmetric utilization of aryldiazonium cations as a source of electrophilic nitrogen. This is achieved through a chiral anion phase-transfer pyrroloindolinization reaction that forms C3-diazenated pyrroloindolines from simple tryptamines and aryldiazonium tetrafluoroborates. The title compounds are obtained in up to 99% yield and 96% ee. The air- and water-tolerant reaction allows electronic and steric diversity of the aryldiazonium electrophile and the tryptamine core. Live and let diazene: Chiral anion phase transfer of aryldiazonium cations has been utilized to prepare C3-diazenated pyrroloindolines. The air- and water-tolerant reaction allows electronic and steric diversity in the aryldiazonium electrophile and the tryptamine core, with the products being obtained in up to 99% yield and 96% ee (MTBE=methyl tert-butyl ether).
- Nelson, Hosea M.,Reisberg, Solomon H.,Shunatona, Hunter P.,Patel, Jigar S.,Toste, F. Dean
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supporting information
p. 5600 - 5603
(2014/06/10)
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- Concise copper-catalyzed synthesis of tricyclic biaryl ether-linked aza-heterocyclic ring systems
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A new method for the synthesis of tricyclic biaryl ether-linked ring systems incorporating seven-, eight-, and nine-membered ring amines is presented. In the presence of catalytic quantities of copper(I), readily accessible acyclic precursors undergo an intramolecular carbon-oxygen bond-forming reaction facilitated by a templating chelating nitrogen atom. The methodology displays a broad substrate scope, is practical, and generates rare and biologically interesting tricyclic heteroaromatic products that are difficult to access by other means.
- Mestichelli, Paola,Scott, Matthew J.,Galloway, Warren R. J. D.,Selwyn, Jamie,Parker, Jeremy S.,Spring, David R.
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supporting information
p. 5448 - 5451
(2013/11/19)
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- Formal total synthesis of (+)-lysergic acid via zinc(II)-mediated regioselective ring-opening reduction of 2-alkynyl-3-indolyloxirane
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Asymmetric formal synthesis of (+)-lysergic acid was achieved with a reductive ring-opening reaction of chiral 2-alkynyl-3-indolyloxirane with NaBH3CN as the key step. With Zn(OTf)2 as an additive, the ring-opening reaction proceeded regioselectively at the 3-position to give the corresponding propargyl alcohol, which was a precursor of the allenic amide for palladium-catalyzed domino cyclization to construct the ergot alkaloid core structure.
- Iwata, Akira,Inuki, Shinsuke,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
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scheme or table
p. 5506 - 5512
(2011/08/22)
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- A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade as a key step
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The indole alkaloid α-cyclopiazonic acid 1 has been synthesised by a route, which features at its core an acid-catalysed cationic cascade cyclisation terminated by a sulfonamide group.
- Griffiths-Jones, Charlotte M.,Knight, David W.
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experimental part
p. 8515 - 8528
(2011/11/29)
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- Studies on the Claisen rearrangements in the indolo[2,3-b]quinoline system
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A study of the effect of substrate structure on a Claisen-aza-Cope reaction is presented including a rationalisation of the reaction outcome using DFT calculations. An asymmetric version of the reaction is also described that is of relevance to a proposed
- Voute, Nicholas,Philp, Douglas,Slawin, Alexandra M. Z.,Westwood, Nicholas J.
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supporting information; experimental part
p. 442 - 450
(2010/02/16)
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- Enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascades
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(Chemical Equation Presented) An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(I)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol % bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.
- Muratore, Michael E.,Holloway, Chloe A.,Pilling, Adam W.,Storer, R. Ian,Trevitt, Graham,Dixon, Darren J.
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supporting information; experimental part
p. 10796 - 10797
(2009/12/03)
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- HETEROARYL AMIDE ANALOGUES
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Compounds, pharmaceutical compositions, and methods of use are disclosed for heteroaryl amide analogues of formula Ia and/or Ib: . In certain embodiments, the heteroaryl amide analogues are agonists and/or ligands of dopamine receptors and may be useful, inter alia, for the treatment of a condition responsive to P2X7 receptor modulation, for example, pain, inflammation, a neurological or neurodegenerative disorder, a cardiovascular disorder, an ocular disorder or an immune system disorder.
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Page/Page column 62
(2009/04/25)
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- HETEROARYL AMIDE ANALOGUES
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Compounds, pharmaceutical compositions, and methods of use are disclosed for heteroaryl amide analogues of formula Ia and/or Ib. In certain embodiments, the heteroaryl amide analogues are agonists and/or ligands of dopamine receptors and may be useful, inter alia, for the treatment of a condition responsive to P2X7 receptor modulation, for example, pain, inflammation, a neurological or neurodegenerative disorder, a cardiovascular disorder, an ocular disorder or an immune system disorder.
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Page/Page column 53
(2009/10/21)
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- Total synthesis of (±)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group
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(Chemical Equation Presented) Ergot alkaloids and their synthetic analogs have been reported to exhibit broad biological activity. We investigated direct construction of the C/D ring system of ergot alkaloids based on palladium-catalyzed domino cyclization of amino allenes. With this biscyclization as the key step, total synthesis of (±)-lysergic acid, (±)-lysergol, and (±)-isolysergol was achieved.
- Inuki, Shinsuke,Oishi, Shinya,Fujii, Nobutaka,Ohno, Hiroaki
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supporting information; experimental part
p. 5239 - 5242
(2009/06/06)
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- INDOLES AS 5-HT6 MODULATORS
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The present invention relates to novel compounds of formula (I) wherein m, n, R0, R1, R2, R3 and R4 are as described herein, to pharmaceutical compositions comprising the compounds, to processes for t
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Page/Page column 85
(2008/06/13)
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- 1,2,3-Thiadiazole substituted pyrazolones as potent KDR/VEGFR-2 kinase inhibitors
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KDR kinase inhibition is considered to play an important role in regulating angiogenesis, which is vital for the survival and proliferation of tumor cells. Recently we disclosed a structure-based kinase inhibitor design strategy which led to the identification of a new class of VEGFR-2/KDR kinase inhibitors bearing heterocyclic substituted pyrazolones as the core template. Instability in a rat S9 preparation and poor iv PK profiles for most of these inhibitors necessitated exploration of new pyrazolones to identify new analogs with improved metabolic stability. Optimization of the heterocyclic moiety led to the identification of the thiadiazole series of pyrazolones (D) as potent VEGFR-2/KDR kinase inhibitors. SAR modifications, kinase selectivity profiling, and structural elements for improved PK properties were explored. Oral bioavailability up to 29% was achieved in the rat. Modeling results based on the Glide XP docking approach supported our postulation regarding the interaction of the lactam segment of the pyrazolones with the hinge region of the KDR kinase.
- Tripathy, Rabindranath,Ghose, Arup,Singh, Jasbir,Bacon, Edward R.,Angeles, Thelma S.,Yang, Shi X.,Albom, Mark S.,Aimone, Lisa D.,Herman, Joseph L.,Mallamo, John P.
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p. 1793 - 1798
(2007/10/03)
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- A synthesis of the welwistatin core
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An approach to the core structure of the microtubule-targeting agent welwistatin is described. The approach utilizes the type 2 intramolecular Diels-Alder reaction, with indole serving as the tether between diene and dienophile, to form the natural produc
- Lauchli, Ryan,Shea, Kenneth J.
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p. 5287 - 5289
(2007/10/03)
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- seco-C/D Ring Analogues of Ergot Alkaloids. Synthesis via Intramolecular Heck and Ring-Closing Metathesis Reactions
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Equation presented. Intramolecular Heck and ring-closing metathesis reactions on key intermediates 10 and 15, respectively, provide efficient entries into seco-C/D ring analogues of Ergot alkaloids 12 and 16, compounds of potential synthetic and biologica
- Kalinin, Alexey V.,Chauder, Brian A.,Rakhit, Suman,Snieckus, Victor
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p. 3519 - 3521
(2007/10/03)
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- Studies towards the synthesis of diazonamide A. Synthesis of the 4-(oxazol-5-ylmethyl) aryltryptamine fragment
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The oxazole substituted 4-aryltryptamine 5, a potential intermediate for the synthesis of the marine natural product diazonamide A 1, has been synthesised. (C) 2000 Elsevier Science Ltd.
- Bagley,Moody,Pepper
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p. 6901 - 6904
(2007/10/03)
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- An attempted total synthesis of lysergic acid via an alkene/n-sulfonylimine cyclization
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Lewis acid-promoted cyclization of the N-tosylimine derived from aldehyde alkene (18) affords an interesting rearranged seven-membered ring tricycle (21) rather than the expected intermediate containing the lysergic acid skeleton.
- Ralbovsky, Janet L.,Scola, Paul M.,Sugino, Eiichi,Burgos-Garcia, Carolina,Weinreb, Steven M.,Parvez, Masood
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p. 1497 - 1512
(2007/10/03)
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