title: Intramolecular vinyl quinone Diels-Alder reactions: asymmetric entry to the cordiachrome core and synthesis of (-)-isoglaziovianol.
abstract: A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (-)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels-Alder reaction and followed by intramolecular nucleophilic interception.
authors: Department of Chemistry and Center of Integrated Protein Science, University of Munich, Butenandtstrasse 5-13 (F4.086), 81377 Munich, Germany.
authors: Florian
authors: F
authors: Löbermann
authors: Lara
authors: L
authors: Weisheit
authors: Dirk
authors: D
authors: Trauner
mesh_terms: D000478:Alkylation; D002384:Catalysis; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011809:Quinones / Q000138:chemical synthesis; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006873:Hydroquinones; D011809:Quinones; D013729:Terpenes; C527505:cordiaquinol I; C586350:isoglaziovianol