110522-48-0Relevant articles and documents
Enantioselective total synthesis of cis-trikentrin B
Lee, Mase,Ikeda, Izumi,Kawabe, Tsuyoshi,Mori, Sayaka,Kanematsu, Ken
, p. 3406 - 3416 (2007/10/03)
Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.
AN ENANTIOCONVERGENT ROUTE TO CARBOCYCLIC NUCLEOSIDES (-)-ARISTEROMYCIN AND (-)-NEPLANOCIN A VIA THE ASYMMETRIC DIELS-ALDER REACTION
Arai, Yoshitsugu,Hayashi, Yoshikazu,Yamamoto, Masatoshi,Takayema, Hiromitsu,Koizumi, Toru
, p. 3133 - 3140 (2007/10/02)
The asymmetric Diels-Alder reaction of (SS)-menthyl-3-(2-pyridylsulphinyl)acrylate (4) with cyclopentadiene gave almost a pure single diastereoisomeric cycloadduct.The cycloadduct was then converted into the central intermediate (+)-(3) which w
A New Route to (-)-Aristeromycin and (-)-Neplanocin A via the Asymmetric Diels-Alder Cycloaddition
Arai, Yoshitsugu,Hayashi, Yoshikazu,Yamamoto, Masatoshi,Takayama, Hiromitsu,Koizumi, Toru
, p. 185 - 186 (2007/10/02)
An enantioselective synthesis of a central intermediate in the synthesis of (-)-aristeromycin and (-)-neplanocin A via the asymmetric Diels-Alder reaction of menthyl (S)s-3-(2-pyridylsulfinyl)propenoate with cyclopentadiene, is described.