title: Synthesis of coronafacic acid via TBAF-assisted elimination of the mesylate and its conversion to the isoleucine conjugate.
abstract: An aldol reaction followed by elimination of the derived mesylate was used to construct the side chain that was designed to afford the cyclohexene ring of coronafacic acid via intramolecular alkylation. Elimination of the mesylate proceeded with TBAF. The alkylation was achieved with t-BuOK in THF, and then hydrolysis afforded coronafacic acid, which upon condensation with unprotected L-isoleucine using ClCO(2)Bu(i) furnished coronafacoyl-L-isoleucine, the L-Ile conjugate.
authors.affiliation: Department of Biomolecular Engineering, Tokyo Institute of Technology, Box B52, Yokohama 226-8501, Japan.
authors.forename: Yusuke
authors.initials: Y
authors.lastname: Kosaki
authors.forename: Narihito
authors.initials: N
authors.lastname: Ogawa
authors.forename: Qian
authors.initials: Q
authors.lastname: Wang
authors.forename: Yuichi
authors.initials: Y
authors.lastname: Kobayashi
mesh_terms: D000478:Alkylation; D007192:Indenes / Q000138:chemical synthesis*; D007532:Isoleucine / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007192:Indenes; D008698:Mesylates; D000644:Quaternary Ammonium Compounds; D007532:Isoleucine; C084266:coronafacic acid; C009405:tetrabutylammonium