title: Syntheses of the hexahydroindene cores of indanomycin and stawamycin by combinations of iridium-catalyzed asymmetric allylic alkylations and intramolecular Diels-Alder reactions.
abstract: Short and concise syntheses of the hexahydroindene cores of the antibiotics indanomycin (X-14547 A) and stawamycin are presented. Key methods used are an asymmetric iridium-catalyzed allylic alkylation, a modified Julia olefination, a Suzuki-Miyaura coupling, and an intramolecular Diels-Alder reaction.
authors.affiliation: Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Gärtner
authors.forename: Gedu
authors.initials: G
authors.lastname: Satyanarayana
authors.forename: Sebastian
authors.initials: S
authors.lastname: Förster
authors.forename: Günter
authors.initials: G
authors.lastname: Helmchen
mesh_terms: D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D007495:Iridium / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D011758:Pyrroles
chemical_list: D000498:Allyl Compounds; D000900:Anti-Bacterial Agents; D007192:Indenes; D007495:Iridium; D009942:Organometallic Compounds; D011714:Pyrans; C114124:indanomycin; D011758:Pyrroles