63555-48-6Relevant academic research and scientific papers
Total synthesis of (-)-ircinianin and (+)-wistarin
Uenishi, Jun'ichi,Kawahama, Reiko,Yonemitsu, Osamu
, p. 1691 - 1701 (2007/10/03)
(-)-Ircinianin (1), a cyclic furanosesterterpenetetronic acid isolated from a marine sponge (genus Ircinia), is synthesized in 17 steps from (S)-2-methylpropane-1,3-diol mono THP ether 10 and 3-furfural. The key step involves a NiCl2-CrCl2-mediated coupling reaction of iodotriene 9 with chiral aldehyde 8 in DMSO and subsequent intramolecular Diels-Alder reaction in one pot. Both reactions proceed very smoothly at room temperature and eventually give the cyclic product 30A possessing the desired cyclic skeleton of 1 in 60% yield. The structure of 30A is determined by X-ray crystallographic analysis. The stereochemistry of Diels-Alder reactions of 7A and another acyclic precursor 7B are discussed. The first total synthesis of (+)-wistarin (2) is accomplished in 55% yield by iodoether ring formation of 1 and hydrogenolysis of the iodide 33A. Based on the coupling constant in the proton NMR spectrum of 33A, the reported structure 2A is revised to 2B.
SYNTHESIS OF (+/-)-IRCINIANIN, A MARINE SPONGE SESTERTERPENE
Takeda, Kei,Sato, Masa-aki,Yoshii, Eiichi
, p. 3903 - 3906 (2007/10/02)
A biogenetic-type synthesis of (+-)-ircinianin (1) via intramolecular Diels-Alder reaction of 2 is described.
