68486-77-1Relevant academic research and scientific papers
Catalytic δ-hydroxyalkynone rearrangement in the stereoselective total synthesis of centrolobine, engelheptanoxides A and C and analogues
Ahmad, Mohammad N.,Chopra, Sidharth,Fernandes, Rodney A.,Kumar, Praveen
, (2021/08/13)
A catalytic stereoselective total synthesis of centrolobine and engelheptanoxides A and C has been completed via a metal-free catalytic δ-hydroxyalkynone rearrangement to 2,3-dihydro-4H-pyran-4-one and diastereoselective hydrogenation to the all syn-2,4,6-trisubstituted pyran strategy. The onliest required chirality was introduced by Jacobsen kinetic resolution, which further directed the diastereoselective hydrogenation. A first stereoselective synthesis of engelheptanoxide A is also accomplished. The analogues and derivatives of centrolobine and engelheptanoxides prepared were evaluated for antitubercular activity against M. tuberculosis H37Rv ATCC 27294.
Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
Pandey, Ganesh,Laha, Ramkrishna,Mondal, Pradip Kumar
supporting information, p. 9689 - 9692 (2019/08/15)
A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.
Convergent total synthesis of (±) myricanol, a cyclic natural diarylheptanoid
Bochicchio,Schiavo,Chiummiento,Lupattelli,Funicello,Hanquet,Choppin,Colobert
, p. 8859 - 8869 (2018/11/30)
Myricanol 1, a constituent of Myrica species, has been reported to lower the levels of the microtubule-associated protein tau (MAPT), whose accumulation plays an important role in some neurodegenerative diseases, such as Alzheimer's disease (AD). Herein w
Flexible Analogues of Azaindole DYRK1A Inhibitors Elicit Cytotoxicity in Glioblastoma Cells
Zhou, Qingqing,Reekie, Tristan A.,Abbassi, Ramzi H.,Venkata, Dinesh Indurthi,Font, Josep S.,Ryan, Renae M.,Rendina, Louis M.,Munoz, Lenka,Kassiou, Michael
, p. 789 - 797 (2018/09/11)
DYRK1A is a novel target for epidermal growth factor receptor (EGFR)-dependent glioblastoma and it represents a promising strategy for cancer therapy. DYRK1A inhibition has been found to promote EGFR degradation in glioblastoma cells by triggering endocyt
Combining spiro-fused cyclohexadienone – tetrahydrofuran ring system with glycine: Asymmetric synthesis of a new class of α-amino acid derivatives
Devi, Runjun,Das, Sajal Kumar
supporting information, p. 2281 - 2283 (2018/05/23)
Herein, we present the asymmetric synthesis of spiro-fused cyclohexadienone – tetrahydrofuran-embedded glycine derivatives as a new class of nonproteinogenic α-amino acid derivatives. Starting from commercially available 2-allylphenols, key β-hydroxy-α-am
Lipase-catalyzed resolution of 1-[4-(benzyloxy)phenyl]hex-5-en-3-ol: Synthesis of (-)-centrolobine
Tadiparthi, Krishnaji,Raghavendra,Kamal, Ahmed
, p. 2321 - 2326 (2017/10/06)
A practical and efficient method for the preparation of homoallylic alcohol and its successful enzymatic resolution has been developed. This lipase-catalyzed resolution process has been optimized with respect to different lipases and solvents. Moreover, M
Lewis Acid Mediated "endo-dig" Hydroalkoxylation-Reduction on Internal Alkynols for the Stereoselective Synthesis of Cyclic Ethers and 1,4-Oxazepanes
Gharpure, Santosh J.,Vishwakarma, Dharmendra S.,Nanda, Santosh K.
supporting information, p. 6534 - 6537 (2017/12/26)
Lewis acid mediated 5/6/7-endo-dig hydroalkoxylation-reduction cascade on internal alkynols gave an expedient, stereoselective synthesis of cyclic ethers and 1,4-oxazepanes. The strategy has been extended to the first examples of hydroalkoxylation-alkyne
Synthesis of tetrahydropyranyl diarylheptanoids from Dioscorea villosa
Kantee, Kawalee,Rukachaisirikul, Vatcharin,Tadpetch, Kwanruthai
supporting information, p. 3505 - 3509 (2016/07/15)
Concise syntheses of four tetrahydropyranyl diarylheptanoids isolated from Dioscorea villosa have been described. The key features include Prins cyclization to construct the tetrahydropyran cores, Keck asymmetric allylation, and Mitsunobu inversion. Optimization of the Prins cyclization conditions in order to minimize racemization has been described. Our syntheses also confirmed the absolute stereochemistry of the natural products.
Stereoselective total synthesis of (3S,5S)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol, (3S,5S)-alpinikatin, and its diastereoisomers
Venkatesham, Kunuru,Purushotham Reddy, Sudina,Chinnababu, Baggu,Suresh Babu, Katragadda
, p. 1307 - 1314 (2015/09/28)
Stereoselective synthesis of the diarylheptanoids, (3S,5S)-1,7-bis(4-hydroxyphenyl)heptane-3,5-diol (1), (3S,5S)-alpinikatin (3), and their diastereoisomers (2 and 4, resp.), was achieved from readily available 4-hydroxybenzaldehyde. The synthetic sequenc
The first stereoselective total synthesis of naturally occurring, bioactive (3R,5R)-1-(4-hydroxyphenyl)-7-phenylheptane-3,5-diol and the synthesis of its enantiomer
Reddy, Parigi Raghavendar,Sudhakar, Chithaluri,Kumar, Jayprakash Narayan,Das, Biswanath
, p. 289 - 295 (2013/03/28)
The first stereoselective total synthesis of the naturally occurring anti-emetic diarylheptanoid (3R,5R)-1-(4-hydroxyphenyl)-7-phenylheptane-3,5-diol (1) was accomplished starting from 4-hydroxybenzaldehyde and involving a Sharpless kinetic resolution and
