154844-47-0Relevant academic research and scientific papers
Acetogenins of annonaceae. Part 86: Synthesis of a highly functionalized precursor of (-)-4-deoxygigantecin, an annonaceous acetogenin
Szlosek, Magali,Peyrat, Jean-Francois,Chaboche, Christophe,Franck, Xavier,Hocquemiller, Reynald,Figadere, Bruno
, p. 337 - 342 (2000)
A highly functionalized precursor of (-)-4-deoxygigantecin possessing six stereogenic centers has been prepared in 14 steps from tridecanal. The key steps are (i) enantioselective aldolization, (ii) diastereoselective C- glycosylation and (iii) diastereoselective aldolization reactions, all of them using 2-trimethylsilyloxyfuran as nucleophile. This strategy would allow us to prepare squamostatin D as well, another acetogenin of Annonaceae possessing two nonadjacent tetrahydrofuran rings and a closely related tetrahydrofuran pattern.
Study of the structure-activity relationships of the acetogenin of annonaceae, muricatacin and analogues
Cave,Chaboche,Figadere,Harmange,Laurens,Peyrat,Pichon,Szlosek,Cotte-Lafitte,Quero
, p. 617 - 623 (2007/10/03)
A study of the structure-cytotoxic activity of the acetogenin of Annonaceae, muricatacin 1, is reported. indeed, muricatacin 1 has shown promising antitumoral activity. Therefore several 5-hydroxy-4-alkcanolides were prepared and then tested against KB and VERO cell lines. A few other analogues were synthesized and tested against both cell lines. Thus this work allowed us to better determine the pharmacophore of the molecule and to propose muricatacin 1 instead of a more complicated acetogenin of Annonaceae as a lead compound in the search for new antineoplastic agents.
Stereocontrolled synthesis of key intermediates in the total synthesis of acetogenins of annonaceae
Figadere, Bruno,Chaboche, Christophe,Peyrat, Jean-Francois,Cave, Andre
, p. 8093 - 8096 (2007/10/02)
(4S, 5S, 8S, 9S)- and (4R, 5S, 8S, 9S)-9-hydroxy-5,8-epoxy-henicosabutanolides 3b and 4b, respectively, have been successfully synthesized from very inexpensive L-glutamic acid. The key step of the synthetic sequence is an alkylation of lactol acetates 5a,b with 2-(trimethylsilyloxy)-furan. Stereochemical relationship assignment of the obtained products were deduced from NMR data, and by chemical correlation.
