Synthesis and Resolution of Substituted Carbohelicenes
datasetposted on 19.06.2015, 00:00 by Kazuteru Usui, Kosuke Yamamoto, Takashi Shimizu, Mieko Okazumi, Biao Mei, Yosuke Demizu, Masaaki Kurihara, Hiroshi Suemune
Three types of racemic helicenyl acetates (1a, 2, and 3a) were synthesized. The synthesis of 2 was achieved by regioselective oxidation using o-iodoxybenzoic acid. The enzymatic kinetic resolution of 1a–3a was studied. The conversion with the highest rate and ee was obtained using 1a as the substrate and lipase Amano PS-IM as the enzyme. The two enantiomers of 1-helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.