title: Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A.
abstract: A Lewis acid catalyzed Nazarov-type cyclization of arylvinylcarbinol has been developed for the asymmetric synthesis of carbotetracyclic core of merosesquiterpenes. The reaction works only in the presence of 2 mol % of Sn(OTf)2 and Bi(OTf)3 in dichloroethane under elevated temperature. The methodology offers the synthesis of a variety of enantioenriched arylvinylcarbinols from commercially available (3aR)-sclareolide 9 in six steps with an eventual concise total synthesis of marine sesquiterpene quinol, akaol A (1a).
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: Nivesh
authors.initials: N
authors.lastname: Kumar
authors.affiliation: Department of Chemistry , Indian Institute of Science Education and Research Bhopal , Bhopal Bypass Road, Bhopal, Madhya Pradesh 462 066, India.
authors.forename: Pradip Kumar
authors.initials: PK
authors.lastname: Mondal
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: D002384:Catalysis; D004224:Diterpenes / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry*; D000432:Methanol / Q000031:analogs & derivatives / Q000737:chemistry*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; D058116:Lewis Acids; D012717:Sesquiterpenes; C000610800:akaol A; C109395:sclareolide; D000432:Methanol