title: Biomimetic total synthesis of ent-penilactone A and penilactone B.
abstract: The total synthesis of ent-penilactone A and penilactone B has been achieved via biomimetic Michael reactions between tetronic acids and o-quinone methides. A five-component cascade reaction between a tetronic acid, formaldehyde, and a resorcinol derivative that generates four carbon-carbon bonds, one carbon-oxygen bond, and two stereocenters in a one-pot synthesis of penilactone A is also reported.
authors.affiliation: School of Chemistry and Physics, University of Adelaide, Adelaide, SA 5005, Australia.
authors.forename: Justin T J
authors.initials: JT
authors.lastname: Spence
authors.forename: Jonathan H
authors.initials: JH
authors.lastname: George
mesh_terms: D032701:Biomimetics; D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D045563:Indolequinones / Q000737:chemistry*; D015394:Molecular Structure; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D045563:Indolequinones; D061065:Polyketides; C587220:penilactone A; C587221:penilactone B; C068040:quinone methide; C003422:tetronic acid