title: Total synthesis of (+)-iresin.
abstract: The first asymmetric total synthesis of (+)-iresin (4), an historically important ent-Drimane sesquiterpene lactone, was realized from aldehyde 3 via cyclic orthoester 6 in 5 steps. Notable transformations in this synthesis include a tandem trifluoroperacetic acid (TFPAA)-mediated Baeyer-Villiger oxidation-olefin epoxidation-epoxy ester cyclization, regioselective Burgess dehydration, and regioselective Fétizon oxidative lactonization.
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Bian-Lin
authors.initials: BL
authors.lastname: Wang
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
authors.forename: Hai-Tao
authors.initials: HT
authors.lastname: Gao
authors.affiliation: †State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.|‡Innovative Drug Research Centre, Chongqing University, Chongqing 401331, P. R. China.
authors.forename: Wei-Dong Z
authors.initials: WD
authors.lastname: Li
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D007783:Lactones; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C437376:drimane; C000603749:iresin