title: Synthetic studies on amaryllidaceae and other terrestrially derived alkaloids.
abstract: The total syntheses of a wide range of terrestrially derived alkaloids, especially ones isolated from members of the Amaryllidaceae family, are described. Two recurring themes associated with these syntheses are the use of two types of building blocks, namely ring-fused cyclopropanes, especially geminally-dihalogenated ones, and enzymatically derived cis-1,2-dihydrocatechols. These have often served as precursors to 2- or 3-halogenated 2-cyclohexen-1-ols that are themselves engaged in cross-coupling reactions, radical addition-elimination processes and/or Claisen- or Overman-type rearrangements so as to construct the highly functionalized six-membered rings associated with the target alkaloids.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Nadia Yuqian
authors.initials: NY
authors.lastname: Gao
authors.forename: Brett D
authors.initials: BD
authors.lastname: Schwartz
authors.forename: Lorenzo V
authors.initials: LV
authors.lastname: White
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis*; D052117:Benzodioxoles / Q000138:chemical synthesis; D003078:Colchicine / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D007546:Isoquinolines / Q000138:chemical synthesis*; D008956:Models, Chemical; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D047151:Amaryllidaceae Alkaloids; D052117:Benzodioxoles; D006576:Heterocyclic Compounds, 4 or More Rings; D026121:Indole Alkaloids; D007546:Isoquinolines; D011804:Quinolines; C409672:aspidospermidine; C524620:erythramine; C434338:grandirubrine; C043049:imerubrine; D003078:Colchicine