244755-91-7Relevant academic research and scientific papers
Approaches Towards the Synthesis of Papulacandin D: Preparation and Structural Elucidation of the Acyl Side Chain
Barrett, Anthony G. M.,Pena, Michael,Willardsen, J. Adam
, p. 1145 - 1146 (1995)
Both degradation and total synthesis from L-(+)-isoleucine are used to establish the absolute stereochemistry of the O-3'-acyl side chain of papulacandin D.
5-Alkyl-1,2,3,4-tetrahydroquinolines, new membrane-interacting lipophilic metabolites produced by combined culture of streptomyces nigrescens and tsukamurella pulmonis
Sugiyama, Ryosuke,Nishimura, Shinichi,Ozaki, Taro,Asamizu, Shumpei,Onaka, Hiroyasu,Kakeya, Hideaki
supporting information, p. 1918 - 1921 (2015/04/27)
Eight novel 5-alkyl-1,2,3,4-tetrahydroquinolines (5aTHQs) bearing different side chains have been isolated from a combined culture of Streptomyces nigrescens HEK616 and Tsukamurella pulmonis TP-B0596. The chemical structures including the absolute configuration were elucidated by spectroscopic analysis and total synthesis. 5aTHQs inhibited the growth of wild-type fission yeast while only weakly inhibiting the growth of several mutant strains synthesizing premature ergosterol. These results demonstrate that 5aTHQs are novel antifungals that may target cell membranes.
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
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).
