title: Toward the synthesis of norzoanthamine: building carbocyclic core by a transannular Michael reaction cascade.
abstract: A 12-step synthesis of the ABC carbocyclic core of norzoanthamine is described. It features an organocatalytic asymmetric intramolecular aldolization to set the stereochemistry of the entire molecule, a fragment coupling by selective alkylation of a bis-enolate, and a transannular Michael reaction cascade for rapid and stereoselective synthesis of the polycyclic core.
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, Texas 77843-3255, USA.
authors.forename: Haoran
authors.initials: H
authors.lastname: Xue
authors.forename: Jiong
authors.initials: J
authors.lastname: Yang
authors.forename: Peddabuddi
authors.initials: P
authors.lastname: Gopal
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012615:Sea Anemones; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D011083:Polycyclic Compounds; D011804:Quinolines; C400280:norzoanthamine