title: Total Synthesis of (-)-Hymenosetin.
abstract: The 3-decalinoyltetramic acid (-)-hymenosetin and its N-methyl analogue were prepared in 11 and 8 steps, respectively, from (+)-citronellal using an intramolecular Diels-Alder reaction as the key step. This method represents the first example for the synthesis of a 3-decalinoyltetramic acid with a free NH moiety. The stereochemistry of the title compound, an unnatural diastereomer, and of a decalin building block was studied in detail using circular dichroism spectroscopy in the IR and UV/VIS freqeuncy range. This allowed to determine the absolute configuration of the natural product and to plan the synthetic route.
authors.affiliation: Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Ulrich
authors.initials: U
authors.lastname: Kauhl
authors.affiliation: Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Lars
authors.initials: L
authors.lastname: Andernach
authors.affiliation: Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Weck
authors.affiliation: Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Louis P
authors.initials: LP
authors.lastname: Sandjo
authors.affiliation: Institut für Biotechnologie und Wirkstoff-Forschung gGmbH (IBWF) , Erwin-Schrödinger-Str. 56, D-67663 Kaiserslautern, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Jacob
authors.affiliation: Institut für Biotechnologie und Wirkstoff-Forschung gGmbH (IBWF) , Erwin-Schrödinger-Str. 56, D-67663 Kaiserslautern, Germany.|Johannes Gutenberg-University Mainz , Institute of Biotechnology and Drug Research, Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Eckhard
authors.initials: E
authors.lastname: Thines
authors.affiliation: Institute of Organic Chemistry, University of Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.
authors.forename: Till
authors.initials: T
authors.lastname: Opatz
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D011760:Pyrrolidinones; C000592499:hymenosetin