title: [Intramolecular cyclization reaction of multiple bonds and its application].
abstract: The cycloaddition and cycloisomerization of the allene with an alkyne, alkene, or an additional allene for construction of various monocyclic and bicyclic ring systems has been developed. The characteristic features of these methods using allene functionality instead of a simple alkene or alkyne include the reaction mode that originated from the double function as well as the high efficiency for the constructions of medium-sized rings. Furthermore, asymmetric formal synthesis of (+)-nakadomarin A and total synthesis of (+)-fawcettimine and (+)-lycoposerramine-B based on highly stereoselective Pauson-Khand reaction of alkene-alkynes were completed.
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kanazawa, Japan. finagaki@p.kanazawa-u.ac.jp
authors.forename: Fuyuhiko
authors.initials: F
authors.lastname: Inagaki
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis; D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis; D055601:Organic Chemistry Phenomena; D010091:Oximes / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D000470:Alkaloids; D000475:Alkenes; D000480:Alkynes; D002243:Carbolines; D006575:Heterocyclic Compounds, 3-Ring; D010091:Oximes; C524731:fawcettimine; C497861:lycoposerramine-B; C476640:nakadomarin A; C025947:propadiene