title: Total Synthesis of (±)-Taiwaniaquinol F and Related Taiwaniaquinoids.
abstract: Total synthesis of (±)-taiwaniaquinol F (1a) has been accomplished via an efficient Lewis acid-catalyzed Nazarov-type cyclization of aryldiallylcarbinols (±)-2e derived from safranal 7. The methodology works under mild conditions using only 2 mol % of metal triflate as catalyst to afford a previously unknown carbotricyclic core sharing an olefin functionality in excellent yield. The aforementioned methodology also offers enough flexibility to complete the total syntheses of various taiwaniaquinoids, including (±)-taiwaniaquinone H (1d), (±)-dichroanone (1e), (±)-5-epi-taiwaniaquinone G (ent-1h), and (±)-taiwaniaquinol B (1b).
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road, Bhopal, Madhya Pradesh 462 066, India.
authors.forename: Badrinath N
authors.initials: BN
authors.lastname: Kakde
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road, Bhopal, Madhya Pradesh 462 066, India.
authors.forename: Pooja
authors.initials: P
authors.lastname: Kumari
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road, Bhopal, Madhya Pradesh 462 066, India.
authors.forename: Alakesh
authors.initials: A
authors.lastname: Bisai
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; C516091:dichroanone; C505702:taiwaniaquinol B; C539836:taiwaniaquinone G; C516088:taiwaniaquinone H