124399-64-0Relevant academic research and scientific papers
Stereoselective Synthesis of the Isomers of Notoincisol A: Assigment of the Absolute Configuration of this Natural Product and Biological Evaluation
Rycek, Lukas,Ticli, Vincenzo,Pyszkowski, Jakob,Latkolik, Simone,Liu, Xin,Atanasov, Atanas G.,Steinacher, Theresa,Bauer, Rudolf,Schuster, Daniela,Dirsch, Verena M.,Schnürch, Michael,Ernst, Margot,Mihovilovic, Marko D.
, p. 2419 - 2428 (2018)
The total syntheses of all stereoisomers of notoincisol A, a recently isolated natural product with potential anti-inflammatory activity, are reported. The asymmetric synthesis was conducted employing a lipase-mediated kinetic resolution, which enables easy access to all required chiral building blocks with the aim of establishing the absolute configuration of the naturally occurring isomer. This was achieved by comparison of optical properties of the isolated compound with the synthetic derivatives obtained. Moreover, an assessment of the biological activity on PPARγ (peroxisome proliferator-activated receptor gamma) as a prominent receptor related to inflammation is reported. Only the natural isomer was found to activate the PPARγ receptor, and this phenomenon could be explained based on molecular docking studies. In addition, the pharmacological profiles of the isomers were determined using the GABAA (gamma-aminobutyric acid A) ion channel receptor as a representative target for allosteric modulation related to diverse CNS activities. These compounds were found to be weak allosteric modulators of the α1β3 and α1β2γ2 receptor subtypes.
Cytotoxic polyacetylenes isolated from the roots and rhizomes of Notopterygium incisum
Zheng, Xikang,Zheng, Xiaoqing,Zhang, Chen,Zhang, Qingying,Jiang, Yong,Tu, Pengfei
, p. 428 - 430 (2019)
Phytochemical investigation on the roots and rhizomes of Notopterygium incisum led to the isolation of a new polyacetylene, notopolyenol A (1), along with thirteen known analogues (2–14). Their structures were elucidated by extensive analyses of NMR and HRMS data, and the absolute configuration of 1 was unambiguously determined as 3R by comparison of its retention time and ECD curve with those of synthetic enantiomers (?)-1 and (+)-1, whose absolute configurations were established by using the modified Mosher's method. Subsequent activity screening revealed that (3S)-1 exhibited the most significant cytotoxicity against MCF-7, H1299, and HepG2 cancer cells with IC50 values of 1.3 μmol/L, 0.6 μmol/L and 1.4 μmol/L, respectively.
Total synthesis of (+)-laurencin
Tsushima,Murai
, p. 4345 - 4348 (1992)
The first total synthesis of (+)-laurencin (1), which is the most representative marine natural product isolated from red algae, is described via intermediates 2-18. Key steps in the synthesis include a facile oxidative preparation of 2, an effective conversion of 9a to 11, and a SmI2-catalyzed elongation reaction of 15, providing 16a.
A general approach to medium ring alkynes by using metathesis of cobalt hexacarbonyl containing dienes
Young, David G. J.,Burlison, Joseph A.,Peters, Ulf
, p. 3494 - 3497 (2003)
The assembly of medium sized rings (7-9) was achieved by using the metathesis of dienes linked by a cobalt hexacarbonyl complexed alkyne with either Grubbs' or Schrock's catalysts. The products of metathesis were subjected to transformations involving the dicobalt hexacarbonyl complexes, for example, decomplexation to liberate cyclic alkynes or Pauson-Khand reaction.
Substituted Tetraethynylethylene–Tetravinylethylene Hybrids
Connor, Kieran P. E.,Horvath, Kelsey L.,Magann, Nicholas L.,Sherburn, Michael S.,Sowden, Madison J.,Westley, Erin
supporting information, p. 977 - 986 (2022/02/03)
A general synthetic approach to molecular structures that are hybrids of tetraethynylethylene (TEE) and tetravinylethylene (TVE) is reported. The synthesis permits the controlled preparation of many previously inaccessible structures, including examples w
Unlocking acyclic π–bond rich structure space with tetraethynylethylene–tetravinylethylene hybrids
Horvath, Kelsey L.,Magann, Nicholas L.,Sowden, Madison J.,Gardiner, Michael G.,Sherburn, Michael S.
supporting information, p. 19746 - 19753 (2019/12/25)
Literature reports describe tetraethynylethylene (TEE) as unstable but tetravinylethylene (TVE) as stable. The stabilities of these two known compounds are reinvestigated, along with those of five unprecedented TEE-TVE hybrid compounds. The five new C10 hydrocarbons possess a core, tetrasubstituted C=C bond carrying all possible combinations of vinyl and ethynyl groups. A unified strategy is described for their synthesis, whereupon cross-conjugated ketones are dibromo-olefinated then cross-coupled. Due to an incorrect but nonetheless widely held belief that acyclic π-bond rich hydrocarbons are inherently unstable, a standardized set of robustness tests is introduced. Whereas only TVE survives storage in neat form, all seven hydrocarbons are remarkably robust in dilute solution, generally surviving exposure to moderate heat, light, air, and acid. The first X-ray crystal structure of TEE is reported. Subgroups of hybrids based upon conformational preferences are identified through electronic absorption spectra and associated computational studies. These new acyclic π-bond rich systems have extensive, untapped potential for the production of stable, conjugated carbon-rich materials.
Studies towards the synthesis of trocheliophorolides
Khomane, Navnath B.,Meshram, Harshadas M.,Rode, Haridas B.
supporting information, p. 2157 - 2160 (2018/05/05)
Total synthesis of trocheliophorolide C epimer is reported. The synthetic strategy involves generation of lactone skeleton and preparation of unsaturated side chain followed by cross-metathesis. The Eglinton oxidative coupling, Cadiot-Chodkiewicz cross-coupling and cross-metathesis are the key reactions used in the synthesis. We also attempted the synthesis of trocheliophorolide D epimer, which includes Cu catalyzed various cross-coupling reactions.
Simultaneous synthesis of both rings of chromenes via a benzannulation/ o -quinone methide formation/electrocyclization cascade
Majumdar, Nilanjana,Korthals, Keith A.,Wulff, William D.
supporting information; experimental part, p. 1357 - 1362 (2012/03/11)
A new route to the chromene ring system has been developed which involves the reaction of an α,β-unsaturated Fischer carbene complex of chromium with a propargyl ether bearing an alkenyl group on the propargylic carbon. This transformation involves a cascade of reactions that begins with a benzannulation reaction and is followed by the formation of an o-quinone methide, and finally results in the emergence of a chromene upon an electrocyclization. This reaction was extended to provide access by employing an aryl carbene complex. This constitutes the first synthesis of chromenes in which both rings of the chromene system are generated in a single step and is highlighted in the synthesis of lapachenole and vitamin E.
Rhodium-catalyzed intra- and intermolecular [5 + 2] cycloaddition of 3-acyloxy-1,4-enyne and alkyne with concomitant 1,2-acyloxy migration
Shu, Xing-Zhong,Li, Xiaoxun,Shu, Dongxu,Huang, Suyu,Schienebeck, Casi M.,Zhou, Xin,Robichaux, Patrick J.,Tang, Weiping
supporting information; experimental part, p. 5211 - 5221 (2012/05/05)
A new type of rhodium-catalyzed [5 + 2] cycloaddition was developed for the synthesis of seven-membered rings with diverse functionalities. The ring formation was accompanied by a 1,2-acyloxy migration event. The five- and two-carbon components of the cycloaddition are 3-acyloxy-1,4-enynes (ACEs) and alkynes, respectively. Cationic rhodium(I) catalysts worked most efficiently for the intramolecular cycloaddition, while only neutral rhodium(I) complexes could facilitate the intermolecular reaction. In both cases, electron-poor phosphite or phosphine ligands often improved the efficiency of the cycloadditions. The scope of ACEs and alkynes was investigated in both the intra- and intermolecular reactions. The resulting seven-membered-ring products have three double bonds that could be selectively functionalized.
Highly enantioselective addition of trimethylsilylacetylene to aldehydes catalyzed by a zinc-amino-alcohol complex
Li, Zhi-Yuan,Wang, Min,Bian, Qing-Hua,Zheng, Bing,Mao, Jian-You,Li, Shuo-Ning,Liu, Shang-Zhong,Wang, Ming-An,Zhong, Jiang-Chun,Guo, Hong-Chao
supporting information; experimental part, p. 5782 - 5786 (2011/06/26)
A fine addition! A highly enantioselective and efficient procedure for the amino-alcohol-zinc-catalyzed addition of trimethylsilylacetylene to aromatic, α,β-unsaturated, and aliphatic aldehydes has been developed (see scheme; R=aryl, alkynyl, or alkyl; TMS=trimethylsilyl; TBDMS=tert- butyldimethylsilyl). The present protocol was successfully applied in the concise synthesis of the natural products marine alkynol and falcarindiol. Copyright
