title: Total synthesis of the proposed structure of trichodermatide A.
abstract: A short total synthesis of the published structure of racemic trichodermatide A is reported. Our synthesis involves a Knoevenagel condensation/Michael addition sequence, followed by the formation of tricyclic hexahydroxanthene-dione and a diastereoselective bis-hydroxylation. The final product, the structure of which was confirmed by X-ray crystallography, has NMR spectra that are very similar, but not identical, to those of the isolated natural product. Quantum chemically computed (13)C shifts agree well with the present NMR measurements.
authors.affiliation: Department of Chemistry and Center for Integrated Protein Science, University of Munich (LMU) , Butenandtstraße 5-13, 81377 München, Germany.
authors.forename: Eddie
authors.initials: E
authors.lastname: Myers
authors.forename: Elena
authors.initials: E
authors.lastname: Herrero-Gómez
authors.forename: Irina
authors.initials: I
authors.lastname: Albrecht
authors.forename: Jennifer
authors.initials: J
authors.lastname: Lachs
authors.forename: Peter
authors.initials: P
authors.lastname: Mayer
authors.forename: Matti
authors.initials: M
authors.lastname: Hanni
authors.forename: Christian
authors.initials: C
authors.lastname: Ochsenfeld
authors.forename: Dirk
authors.initials: D
authors.lastname: Trauner
mesh_terms: D002247:Carbon Isotopes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D018942:Macrolides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D002247:Carbon Isotopes; D018942:Macrolides; C527910:trichodermatide A