title: Biomimetic synthesis of dimeric metabolite acremine G via a highly regioselective and stereoselective Diels-Alder reaction.
abstract: The dimeric metabolite acremine G was synthesized featuring a highly regioselective and stereoselective Diels-Alder reaction between a TBS-protected hydroquinone diene and a structurally related alkenyl quinone. The major endo [4 + 2] adduct slowly transforms to acremine G by the atmospheric air under the deprotection conditions (in situ generated HF).
authors.affiliation: Department of Chemistry, University of Crete, Voutes 71003 Iraklion, Greece.
authors.forename: Elias
authors.initials: E
authors.lastname: Arkoudis
authors.forename: Ioannis N
authors.initials: IN
authors.lastname: Lykakis
authors.forename: Charis
authors.initials: C
authors.lastname: Gryparis
authors.forename: Manolis
authors.initials: M
authors.lastname: Stratakis
mesh_terms: D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics / Q000379:methods; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D016227:Benzoquinones; C527633:acremine G