title: A chemoenzymatic total synthesis of the protoilludane aryl ester (+)-armillarivin.
abstract: The title natural product, 1, has been synthesized in 20 steps from the enantiomerically pure cis-1,2-dihydrocatechol 2, itself obtained through the whole-cell biotransformation of toluene. The pivotal steps in the reaction sequence involve a Diels-Alder cycloaddition reaction between diene 2 and cyclopentenone (3) and the photochemically promoted 1,3-acyl rearrangement of the bicyclo[2.2.2]oct-4-en-1-one 20 derived from the cycloadduct 4.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200, Australia.
authors.forename: Brett D
authors.initials: BD
authors.lastname: Schwartz
authors.forename: Eliška
authors.initials: E
authors.lastname: Matoušová
authors.forename: Richard
authors.initials: R
authors.lastname: White
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D004952:Esters; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D003517:Cyclopentanes; D004952:Esters; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C506221:protoilludane; C071426:armillarivin; C013905:cyclopentenone