Stereoselective total synthesis of ent-EI-1941-2 and Epi-ent-EI-1941-2.
The first asymmetric total syntheses of ent-EI-1941-2 and epi-ent-EI-1941-2 have been accomplished, starting from a chiral epoxy iodoquinone 6, a key intermediate in our total syntheses of epoxyquinols A and B. A key step in the preparation of ent-EI-1941-2 is an intramolecular carboxypalladation via a 6-endo cyclization mode, followed by beta-hydride elimination, while carboxymercuration is a key step in the synthesis of epi-ent-EI-1941-2. [reaction: see text]
Shoji
Mitsuru
M
Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
Uno
Takao
T
Hayashi
Yujiro
Y
D003500:Cyclization; D003512:Cyclohexanones / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D011809:Quinones / Q000737:chemistry; D013237:Stereoisomerism
D003512:Cyclohexanones; C476114:EI-1941-2; D004852:Epoxy Compounds; D011809:Quinones