title: Multicomponent Double Diels-Alder/Nazarov Tandem Cyclization of Symmetric Cross-Conjugated Diynones to Generate [6-5-6] Tricyclic Products.
abstract: The construction of complex polycyclic terpenoid products in an efficient and step-economical manner using multicomponent and tandem processes is highly valuable. Herein, we report a tandem cyclization sequence that initiates with a multicomponent double Diels-Alder reaction of cross-conjugated diynones, followed by a Nazarov cyclization to efficiently produce [6-5-6] tricyclic products with excellent regio- and diastereoselectivity. This methodology generates five new carbon-carbon bonds, three rings, quaternary or vicinal quaternary carbons, and stereogenic centers in a one-pot reaction.
authors.affiliation: Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, NV, 89557, USA.
authors.forename: Rachael A
authors.initials: RA
authors.lastname: Carmichael
authors.affiliation: Department of Chemistry, University of Nevada, Reno, 1664 N. Virginia St., Reno, NV, 89557, USA. wchalifoux@unr.edu.
authors.forename: Wesley A
authors.identifier: http://orcid.org/0000-0002-6849-6829
authors.initials: WA
authors.lastname: Chalifoux
mesh_terms: D002244:Carbon / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D058116:Lewis Acids / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D058116:Lewis Acids; D013729:Terpenes; D002244:Carbon
keywords: Diels-Alder reaction; Nazarov reaction; multicomponent reaction; tandem reaction; terpenes