title: A novel, versatile D-->BCD steroid construction strategy, illustrated by the enantioselective total synthesis of estrone.
abstract: A general steroid synthesis is presented that relies on prior formation of three stereogenic centers (C8, C13, and C14) on a D ring template, followed by C- and B-ring cyclizations. The assembly of the key D ring template, achieved by a 3-component conjugate addition/alkylation process, allows introduction of structural variety as required. The method is illustrated by the total synthesis of estrone via a C-ring closing metathesis and a B-ring Heck cyclization.
authors.affiliation: University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ, United Kingdom.
authors.forename: Vincent
authors.initials: V
authors.lastname: Foucher
authors.forename: Benedetta
authors.initials: B
authors.lastname: Guizzardi
authors.forename: Marinus B
authors.initials: MB
authors.lastname: Groen
authors.forename: Mark
authors.initials: M
authors.lastname: Light
authors.forename: Bruno
authors.initials: B
authors.lastname: Linclau
mesh_terms: D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D004970:Estrone / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D004970:Estrone