22299-70-3Relevant academic research and scientific papers
Synthesis of Well-Defined Oligo(2,5-dialkoxy-1,4-phenylene vinylene)s with Chiral End Groups: Unique Helical Aggregations Induced by the Chiral Chain Ends
Yorsaeng, Sakkawet,Kato, Yuka,Tsutsumi, Ken,Inagaki, Akiko,Kitiyanan, Boonyarach,Fujiki, Michiya,Nomura, Kotohiro
supporting information, p. 16764 - 16768 (2015/11/16)
Oligo(2,5-dialkoxy-1,4-phenylenevinylene)s containing three different chiral alkoxy substituents on the phenyl end groups with structurally regular (all trans) controlled repeat units have been prepared; these compounds showed highly enhanced aggregation-induced circular dichroism (AICD; formation of supramolecular polymers), and an inversion of the CD signal was observed even with the same end groups under certain conditions.
Stereoselective synthesis of an alarm pheromone of Grematogaster ants using (4S)-4-benzyloxazolidinone as chiral auxiliary
Zhou,Lu,Chen,Yang
experimental part, p. 83 - 85 (2010/08/20)
(S)-6-Methyl-3-octanone, a component of the alarm pheromone of Grematogaster ants, was synthesized through a key step of stereoselective Michael addition reaction using (4S)-4-benzyloxazolidinone as chiral auxiliary. The target product was obtained with a
Synthetic study of polyoxypeptin: Stereoselective synthesis of the acyl side-chain segment
Noguchi,Yamada,Uchiro,Kobayashi
, p. 7499 - 7502 (2007/10/03)
The first synthesis of the acyl side-chain segment of polyoxypeptin, a potent inducer of apoptosis in human pancreatic carcinoma AsPC-1, was accomplished. The key feature of the present synthesis is the stereospecific palladium-catalyzed hydrogenolysis of
Total synthesis and structural elucidation of the antifungal agent papulacandin D
Barrett, Anthony G. M.,Pena, Michael,Willardsen, J. Adam
, p. 1082 - 1100 (2007/10/03)
Condensation of the aryllithium reagents, prepared from the bromides 10 and 11 and tert-butyllithium, with lactone 19 and acid-catalyzed spirocyclization gave the papulacandin spiroketals 14 and 15. Subsequent protection using di-tert-butylsilyl bis(trifluoromethanesulfonate) gave the diols 31 and 30. Isoleucine (37) was converted using a double Wittig reaction sequence and propargylation of the intermediate aldehyde 46 into the alkynol 47. Separation of the C-7 epimers of 47 was achieved using kinetic resolution via Sharpless epoxidation. Both alkynol epimers 53 and 57 were converted into the papulacandin side chain esters 65 and 66 using a hydrozirconation and palladium(0)-catalyzed coupling sequence. Comparisons of Mosher ester derivatives of 65 and 66 with the Mosher ester derivative of the natural papulacandin side chain and further degradation were consistent with the stereochemistry of the natural product being 7S,14S. Esterification of the spiroketals with the mixed anhydride 70 and global deprotection gave papulacandin D (1).
