title: Biomimetic total synthesis of (±)-yezo'otogirin A.
abstract: The total synthesis of yezo'otogirin A has been achieved via a biosynthetically-inspired strategy. Diastereoselective synthesis of pre-yezo'otogirin A, the proposed biosynthetic pre-cursor of yezo'otogirin A, was accomplished in eight steps from 3-ethoxy-2-cyclohexenone. A biomimetic oxidative radical cyclization was then used to construct the unique tricyclic ring system of yezo'otogirin A. The synthesis showcases the ability of biomimetic radical cyclizations to generate complex natural products from unprotected intermediates.
authors.affiliation: Department of Chemistry, University of Adelaide, Adelaide, SA 5005, Australia. jonathan.george@adelaide.edu.au.
authors.forename: Hiu C
authors.initials: HC
authors.lastname: Lam
authors.forename: Kevin K W
authors.initials: KK
authors.lastname: Kuan
authors.forename: Jonathan H
authors.initials: JH
authors.lastname: George
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D006575:Heterocyclic Compounds, 3-Ring