Synthesis and Resolution of Substituted [5]Carbohelicenes

Kazuteru Usui; Kosuke Yamamoto; Takashi Shimizu; Mieko Okazumi; Biao Mei; Yosuke Demizu; Masaaki Kurihara; Hiroshi Suemune

doi:10.1021/acs.joc.5b00759

Synthesis and Resolution of Substituted [5]Carbohelicenes

Kazuteru Usui, Kosuke Yamamoto, Takashi Shimizu, Mieko Okazumi, Biao Mei, Yosuke Demizu, Masaaki Kurihara, Hiroshi Suemune

Chemo-Pharmaceutical Sciences

Research output: Contribution to journal › Article

19 Citations (Scopus)

Abstract

Three types of racemic [5]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-[5]helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.

Original language	English
Pages (from-to)	6502-6508
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	80
Issue number	12
DOIs	https://doi.org/10.1021/acs.joc.5b00759
Publication status	Published - Jun 19 2015

All Science Journal Classification (ASJC) codes

Organic Chemistry

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title = "Synthesis and Resolution of Substituted [5]Carbohelicenes",

abstract = "Three types of racemic [5]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-[5]helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.",

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T1 - Synthesis and Resolution of Substituted [5]Carbohelicenes

AU - Usui, Kazuteru

AU - Yamamoto, Kosuke

AU - Shimizu, Takashi

AU - Okazumi, Mieko

AU - Mei, Biao

AU - Demizu, Yosuke

AU - Kurihara, Masaaki

AU - Suemune, Hiroshi

PY - 2015/6/19

Y1 - 2015/6/19

N2 - Three types of racemic [5]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-[5]helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.

AB - Three types of racemic [5]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-[5]helicenol 3b were separated using (1S)-10-camphorsulfonyl chloride as the chiral resolving agent.

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