title: Total synthesis of (+)-(2'S,3'R)-zoapatanol exploiting the B-alkyl Suzuki reaction and the nucleophilic potential of the sulfinyl group.
abstract: A stereoselective synthesis of the diterpenoid oxepane (+)-zoapatanol is described. The key steps include a B-alkyl Suzuki cross-coupling reaction for the stereoselective synthesis of trisubstituted alkenes, creation of the two stereogenic centers on the oxepane ring by heterofunctionalization of an alkene through substrate control exploiting the nucleophilic potential of an intramolecular sulfinyl group, and transformation of a β-hydroxy sulfoxide into a terminal alkene.
authors.affiliation: Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, India. sraghavan@iict.res.in
authors.forename: Sadagopan
authors.initials: S
authors.lastname: Raghavan
authors.forename: Vaddela
authors.initials: V
authors.lastname: Sudheer Babu
mesh_terms: D003270:Contraceptive Agents / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003270:Contraceptive Agents; D010082:Oxepins; C442248:zoapatanol