title: Assembly of Terpenoid Cores by a Simple, Tunable Strategy.
abstract: Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid-like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.
authors.affiliation: Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611-7200, USA.
authors.forename: Ouidad
authors.initials: O
authors.lastname: Lahtigui
authors.affiliation: Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611-7200, USA.
authors.forename: Fabien
authors.initials: F
authors.lastname: Emmetiere
authors.affiliation: Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611-7200, USA.
authors.forename: Wei
authors.initials: W
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611-7200, USA.
authors.forename: Liban
authors.initials: L
authors.lastname: Jirmo
authors.affiliation: Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611-7200, USA.
authors.forename: Samira
authors.initials: S
authors.lastname: Toledo-Roy
authors.affiliation: Department of Chemistry and Physics, Arkansas State University, Jonesboro, AR, 72467, USA.
authors.forename: John C
authors.initials: JC
authors.lastname: Hershberger
authors.affiliation: Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611-7200, USA.
authors.forename: Jocelyn M
authors.initials: JM
authors.lastname: Macho
authors.affiliation: Department of Chemistry, University of Florida, PO Box 117200, Gainesville, FL, 32611-7200, USA.
authors.forename: Alexander J
authors.identifier: 0000-0002-8182-9464
authors.initials: AJ
authors.lastname: Grenning
keywords: Knoevenagel adducts; [3,3] Cope rearrangement; allylic alkylation; deconjugative alkylation; terpene synthesis