title: Synthesis of an Isomer of the Decalinoyltetramic Acid Methiosetin by a Stereocontrolled IMDA Reaction of a Metal-Chelated 3-Trienoyltetramate.
abstract: An isomer of the 3-decalinoyltetramic acid methiosetin was synthesized for the first time. The decalin moiety was established by a late-stage intramolecular Diels-Alder cyclization catalyzed by Me2AlCl or La(OTf)3. Its high diastereoselectivity arose from stereoinduction by a well-defined metal O,O-chelate complex of the 3-acyltetramic acid moiety. The nature of the metal and the bulkiness of the residues at the tetramic acid chelator are decisive for the stereochemical outcome.
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth , 95440 Bayreuth, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Winterer
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth , 95440 Bayreuth, Germany.
authors.forename: Karl
authors.initials: K
authors.lastname: Kempf
authors.affiliation: Organic Chemistry Laboratory, University Bayreuth , 95440 Bayreuth, Germany.
authors.forename: Rainer
authors.initials: R
authors.lastname: Schobert