65474-82-0Relevant academic research and scientific papers
Photoredox Generated Vinyl Radicals: Synthesis of Bisindoles and β-Carbolines
Chalotra, Neha,Ahmed, Ajaz,Rizvi, Masood Ahmad,Hussain, Zakir,Ahmed, Qazi Naveed,Shah, Bhahwal Ali
, p. 14443 - 14456 (2018/12/11)
A photoredox catalyzed approach enabling use of alkynes as surrogate of 2-oxoaldehydes/1,2-diones is reported. The method overcomes the difficulty associated with application of unsubstituted aliphatic α-oxoaldehydes, which has hitherto limited their general use. Indoles, tryptamine, and tryptophan methyl ester participated in the reaction to give a variety of α-oxo based analogues. Quantum yield investigations support a radical chain mechanism.
The Broad Aryl Acid Specificity of the Amide Bond Synthetase McbA Suggests Potential for the Biocatalytic Synthesis of Amides
Petchey, Mark,Cuetos, Anibal,Rowlinson, Benjamin,Dannevald, Stephanie,Frese, Amina,Sutton, Peter W.,Lovelock, Sarah,Lloyd, Richard C.,Fairlamb, Ian J. S.,Grogan, Gideon
supporting information, p. 11584 - 11588 (2018/09/10)
Amide bond formation is one of the most important reactions in pharmaceutical synthetic chemistry. The development of sustainable methods for amide bond formation, including those that are catalyzed by enzymes, is therefore of significant interest. The ATP-dependent amide bond synthetase (ABS) enzyme McbA, from Marinactinospora thermotolerans, catalyzes the formation of amides as part of the biosynthetic pathway towards the marinacarboline secondary metabolites. The reaction proceeds via an adenylate intermediate, with both adenylation and amidation steps catalyzed within one active site. In this study, McbA was applied to the synthesis of pharmaceutical-type amides from a range of aryl carboxylic acids with partner amines provided at 1–5 molar equivalents. The structure of McbA revealed the structural determinants of aryl acid substrate tolerance and differences in conformation associated with the two half reactions catalyzed. The catalytic performance of McbA, coupled with the structure, suggest that this and other ABS enzymes may be engineered for applications in the sustainable synthesis of pharmaceutically relevant (chiral) amides.
Iodine-mediated oxidative Pictet-Spengler reaction using terminal alkyne as the 2-oxoaldehyde surrogate for the synthesis of 1-aroyl-β-carbolines and fused-nitrogen heterocycles
Dighe, Shashikant U.,Samanta, Surya K.,Kolle, Shivalinga,Batra, Sanjay
, p. 2455 - 2467 (2017/04/03)
An efficient iodine-mediated oxidative Pictet-Spengler reaction in dimethyl sulphoxide (DMSO) using terminal alkynes as the 2-oxoaldehyde surrogate for the synthesis of aryl (9H-pyrido[3,4-b]indol-1-yl)methanones is described. The scope of the protocol includes the total synthesis of Fascaplysin, Eudistomins Y1 and Y2. The methodology is extended for preparing pyrrolo[1,2-a]-quinoxaline and indolo[1,5-a]quinoxaline derivatives. The utility of 1-aroyl-β-carbolines was demonstrated by performing palladium-catalyzed β-carboline directed ortho-C(sp2)-H functionalization of the phenyl ring with thiomethyl (SMe) group using DMSO as source and for accessing 4-aryl-canthin-6-ones.
Unexplored reactivity of 2-oxoaldehydes towards Pictet-Spengler conditions: Concise approach to β-carboline based marine natural products
Battini, Narsaiah,Padala, Anil K.,Mupparapu, Nagaraju,Vishwakarma, Ram A.,Ahmed, Qazi Naveed
, p. 26258 - 26263 (2014/07/08)
Novel reactions under Pictet-Spengler conditions between tryptophan methyl ester/tryptamine and 2-oxoaldehydes have been developed and successfully utilized for the total synthesis of Merinacarboline (A and B), Eudistomin Y1, Pityriacitrin B, Pityriacitrin, Fascaplysin and analogues.
A cascade coupling strategy for one-pot total synthesis of β-carboline and isoquinoline-containing natural products and derivatives
Zhu, Yan-Ping,Liu, Mei-Cai,Cai, Qun,Jia, Feng-Cheng,Wu, An-Xin
supporting information, p. 10132 - 10137 (2013/09/02)
Multi-birds with one stone: A cascade coupling strategy was developed for the synthesis of β-carbolines. The method can direct the synthesis of β-carboline and isoquinoline-containing natural products with high yields. Moreover, this protocol can also be further applied towards the total synthesis of natural products fascaplysin and papaverin (see scheme). Copyright
Tandem iodine-mediated oxidations of tetrahydro-β-carbolines: Total synthesis of eudistomins Y1-Y7
Panarese, Joseph D.,Waters, Stephen P.
supporting information, p. 3428 - 3431 (2013/06/05)
An efficient iodine-mediated oxidation of tetrahydro-β-carbolines is described to yield aromatic β-carboline products with tandem C-H oxidation. The utility of the method was demonstrated in total syntheses of the alkaloids eudistomins Y1-Y7. The Royal Society of Chemistry.
