title: Stereoselective synthesis of the ABC ring system of norzoanthamine.
abstract: [reaction: see text] An efficient synthesis of enone 4, representing the ABC ring motif of norzoanthamine, is presented. The crucial C22 quaternary center was introduced via a stereoselective methylation of enone 8. The trans-anti-trans relative configuration of the ABC framework of 4 was installed via a sequence of reactions that included a hydroboration and a modified Robinson annulation.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
authors.forename: Subhash
authors.initials: S
authors.lastname: Ghosh
authors.forename: Fatima
authors.initials: F
authors.lastname: Rivas
authors.forename: Derek
authors.initials: D
authors.lastname: Fischer
authors.forename: Miguel A
authors.initials: MA
authors.lastname: González
authors.forename: Emmanuel A
authors.initials: EA
authors.lastname: Theodorakis
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D000818:Animals; D037421:Anthozoa; D001381:Azepines / Q000138:chemical synthesis / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D011804:Quinolines; C400280:norzoanthamine