title: Total synthesis of plukenetione A.
abstract: We describe an alkylative dearomatization/acid-mediated adamantane annulation sequence that allows facile access to type A polyprenylated acylphloroglucinol natural products including plukenetione A. Introduction of the 2-methyl-1-propenyl moiety was achieved via stereodivergent S(N)2 and S(N)1 cyclizations of allylic alcohol substrates.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, USA.
authors.forename: Qiang
authors.initials: Q
authors.lastname: Zhang
authors.forename: Branko
authors.initials: B
authors.lastname: Mitasev
authors.forename: Ji
authors.initials: J
authors.lastname: Qi
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D000478:Alkylation; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis*
chemical_list: D011083:Polycyclic Compounds; C534123:plukenetione A