944335-22-2Relevant 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.
Total synthesis and stereochemical assignment of nostosin B
Wang, Xiaoji,Feng, Junmin,Xu, Zhengshuang,Ye, Tao,Meng, Yi,Zhang, Zhiyu
, (2017/04/06)
Nostosins A and B were isolated from a hydrophilic extract of Nostoc sp. strain from Iran, which exhibits excellent trypsin inhibitory activity. Nostosin A was the most potent natural tripeptide aldehyde as trypsin inhibitor up to now. Both R- and S-2-hydroxy-4-(4-hydroxy-phenyl)butanoic acid (Hhpba) were prepared and incorporated into the total synthesis of nostosin B, respectively. Careful comparison of the NMR spectra and optical rotation data of synthetic nostosin B (1a and 1b) with the natural product led to the unambiguous identification of the R-configuration of the Hhpba fragment, which was further confirmed by co-injection with the authentic sample on HPLC using both reversed phase column and the chiral AD-RH column.
Complete synthesis method of natural product Nostosin B
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, (2017/01/17)
The invention discloses a complete synthesis method of a natural product Nostosin B, and belongs to the technical field of organic synthesis. According to the synthesis method, complete synthesis of the natural product Nostosin B is completed by natural amino acid L-isoleucine, arginine and a non-natural compound 2 which are cheap and easy to obtain through peptide coupling and using of various of functional group protecting groups. The natural product Nostosin B is prepared through the complete synthesis method for the first time. The synthesis method has the advantages of being simple, convenient, feasible, easy to operate and high in yield.
New synthesis method of two enantiomers of 4-(4-(benzyloxy)phenyl)-2-hydroxybutyric acid
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, (2017/02/28)
The invention discloses a new synthesis method of two enantiomers of 4-(4-(benzyloxy)phenyl)-2-hydroxybutyric acid. The invention adopts cheap and easily available p-hydroxy benzaldehyde and (R)-(+)-2, 2-dimethyl-1, 3-dioxolane-4-formaldehyde as initial raw materials to conduct total synthesis study on brand new compounds (R)-4-(4-(benzyloxy)phenyl)-2-hydroxybutyric acid and (S)-4-(4-(benzyloxy)phenyl)-2-benzyl hydroxybutyric acid. The invention uses an asymmetric synthesis method to synthesize two molecules by one route, fills the blank, and provides convenience for future scientific research.
Stereoselective total synthesis of phenolic nonadecanediol
Chinnababu, Baggu,Purushotham Reddy, Sudina,Venkatesham, Kunuru,Chandra Rao, Dasireddi,Venkateswarlu, Yenamandra
, p. 613 - 618 (2014/06/09)
A simple and highly efficient synthetic route has been developed for synthesis of 1-(4-hydroxyphenyl)nonadecane-3,5-diol (1). The two stereogenic centers were generated by employing proline asymmetric α-hydroxylation (MacMillan α-hydroxylation), Jacobsen's hydrolytic kinetic resolution (HKR), and, finally, Yamaguchi oxirane opening as key steps (Scheme 2). Copyright
An efficient approach to the stereoselective synthesis of 2,6-disubstituted dihydropyrans via stannyl-Prins cyclization
Dziedzic, Magdalena,Furman, Bart?omiej
, p. 678 - 681 (2008/09/16)
A general method has been developed for the stereoselective construction of 2,6-disubstituted dihydropyrans based on the Lewis acid-catalyzed intramolecular reactions of oxocarbenium ions with vinylstannanes. This novel methodology was applied to the enan
Asymmetric synthesis of (R)-(-)-rhododendrol, the aglycone of the hepatoprotective agent rhododendrin
Sabitha, Gowravaram,Thirupathaiah,Yadav
, p. 1683 - 1688 (2008/02/01)
Starting from 2,3-O-isopropylidene-D-glyceraldehyde (3) as chiral material, (R)-(-)-rhododendrol 2, the aglycone of the naturally occurring rhododendrin 1 was synthesized. Copyright Taylor & Francis Group, LLC.
