133617-19-3Relevant academic research and scientific papers
Synthesis and evaluation of novel, selective, functionalized γ-butyrolactones as sigma-2 ligands
Blass, Benjamin E.,Blattner, Kevin M.,Canney, Daniel J.,Gao, Rong,Gordon, John C.,Pippin, Douglas A.
, p. 337 - 349 (2022/01/19)
The sigma-2 (σ2) receptor was discovered nearly 40 years ago and was recently identified as the Transmembrane Protein 97 (TMEM97, also known as MAC30 (Meningioma-associated protein)). Aberrant σ2 activity has been linked to diseases
Complex Polyheterocycles and the Stereochemical Reassignment of Pileamartine A via Aza-Heck Triggered Aryl C-H Functionalization Cascades
Bower, John F.,Caiger, Lewis,García-Cárceles, Javier,Hazelden, Ian R.,Jones, Benjamin T.,Langer, Thomas,Lewis, Richard J.
, p. 15593 - 15598 (2021/10/12)
Structurally complex benzo- and spiro-fused N-polyheterocycles can be accessed via intramolecular Pd(0)-catalyzed alkene 1,2-aminoarylation reactions. The method uses N-(pentafluorobenzoyloxy)carbamates as the initiating motif, and this allows aza-Heck-type alkene amino-palladation in advance of C-H palladation of the aromatic component. The chemistry is showcased in the first total synthesis of the complex alkaloid (+)-pileamartine A, which has resulted in the reassignment of its absolute stereochemistry.
First Stereoselective Total Synthesis of Modiolin
Rao, G. Padma,Mohan, B. Sathish,Siddaiah
, p. 2028 - 2031 (2021/01/13)
Abstract: The first stereoselective total synthesis of the linear pentaketide Modiolin has been performed via Jacobsen’ hydrolytic kinetic resolution and 2C-Wittig homologation as key steps.
Total Synthesis and Cytotoxic Activity of 5′-Hydroxyzearalenone and 5′β-Hydroxyzearalenone
Thiraporn, Aticha,Rukachaisirikul, Vatcharin,Iawsipo, Panata,Somwang, Tatiyar,Tadpetch, Kwanruthai
, p. 7133 - 7147 (2017/12/28)
An efficient and convergent synthesis of 5′-hydroxyzearalenone and 5′β-hydroxyzearalenone, 14-membered β-resorcylic acid lactone (RAL) natural products, has been achieved in a longest linear sequence of 19 steps, and a total of 29 steps, starting from commercially available 5-hexen-1-ol and methyl 2-(3,5-dimethoxyphenyl)acetate. The key features of our synthesis include a Jacobsen hydrolytic kinetic resolution, a Mitsunobu esterification and (an E)-selective ring-closing metathesis (RCM). Our synthesis also highlights the utility of the acetal protecting group for the resorcylate moiety, and its compatibility with RCM reactions for the synthesis of 14-membered RALs. The cytotoxic activity of both synthetic compounds was evaluated against seven human cancer cell lines. 5′-Hydroxyzearalenone shows more potent cytotoxic activity against most of the cancer cell lines tested than its epimer, 5′β-hydroxyzearalenone. Both compounds show significant cytotoxic activity against the C33A cervical cancer cell line, with IC50 values of 21.33 ± 6.43 μm and 16.00 ± 12.17 μm, respectively.
Synthesis of (-)-isosolenopsin using diastereoselective aminopalladation
Takemoto, Yukiko,Hattori, Yasunao,Makabea, Hidefumi
, p. 286 - 296 (2017/03/27)
Concise synthesis of (-)-isosolenopsin, a piperidine alkaloid isolated from the fire ants (Solenopsis) was achieved. 2,6-Disubstituted piperidine ring of (-)-isosolenopsin was constructed using diastereoselective aminopalladation. Chain elongation using G
Stereoselective synthesis of dendrodolide-L
Bujaranipalli, Sheshurao,Das, Saibal
, p. 254 - 260 (2017/03/01)
An efficient stereoselective total synthesis of 12-membered macrolide dendrodolide L has been achieved. The key reactions involved are Keck asymmetric allylation, Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Mitsunobu reaction and ring-closing metathesis reaction.
Cu-Catalyzed cross-coupling reactions of epoxides with organoboron compounds
Lu, Xiao-Yu,Yang, Chu-Ting,Liu, Jing-Hui,Zhang, Zheng-Qi,Lu, Xi,Lou, Xin,Xiao, Bin,Fu, Yao
supporting information, p. 2388 - 2391 (2015/02/05)
A copper-catalyzed cross-coupling reaction of epoxides with arylboronates is described. This reaction is not limited to aromatic epoxides, because aliphatic epoxides are also suitable substrates. In addition, N-sulfonyl aziridines can be successfully converted into the products. This reaction provides convenient access to β-phenethyl alcohols, which are valuable synthetic intermediates.
Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors
Florence, Gordon J.,Fraser, Andrew L.,Gould, Eoin R.,King, Elizabeth F. B.,Menzies, Stefanie K.,Morris, Joanne C.,Tulloch, Lindsay B.,Smith, Terry K.
, p. 2548 - 2556 (2015/04/22)
Neglected tropical diseases remain a serious global health concern. Here, a series of novel bis-tetrahydropyran 1,4-triazole analogues based on the framework of chamuvarinin, a polyketide natural product isolated from the annonaceae plant species are deta
Non-natural Acetogenin Analogues as Potent Trypanosoma brucei Inhibitors
Florence, Gordon J.,Fraser, Andrew L.,Gould, Eoin R.,King, Elizabeth F. B.,Menzies, Stefanie K.,Morris, Joanne C.,Tulloch, Lindsay B.,Smith, Terry K.
, p. 2548 - 2556 (2015/08/24)
Neglected tropical diseases remain a serious global health concern. Here, a series of novel bis-tetrahydropyran 1,4-triazole analogues based on the framework of chamuvarinin, a polyketide natural product isolated from the annonaceae plant species are deta
Stereoselective total synthesis of polyketide lactone, (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone
Sabitha, Gowravaram,Gopal, Peddabuddi,Yadav, Jhillu S.
scheme or table, p. 1493 - 1499 (2009/12/01)
The total synthesis of lactone 1 has been described. The convergent asymmetric synthesis relies on the use of an Evans' syn-aldol, chain extension with lithio tert-butyl acetate, and the stereoselective reduction of a ketone as the key reactions.
