Enantioselective Organocatalytic Construction of Hexahydropyrroloindole by Means of α-Alkylation of Aldehydes Leading to the Total Synthesis of (+)-Gliocladin C

Authors

  • Jin Song,

    1. Hefei National Laboratory for Physical Sciences, Microscale Joint Laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P.R. China), Fax: (+86) 551-3606266
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  • Chang Guo,

    1. Hefei National Laboratory for Physical Sciences, Microscale Joint Laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P.R. China), Fax: (+86) 551-3606266
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  • Arafate Adele,

    1. Hefei National Laboratory for Physical Sciences, Microscale Joint Laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P.R. China), Fax: (+86) 551-3606266
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  • Dr. Hao Yin,

    1. Hefei National Laboratory for Physical Sciences, Microscale Joint Laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P.R. China), Fax: (+86) 551-3606266
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  • Prof. Liu-Zhu Gong

    Corresponding author
    1. Hefei National Laboratory for Physical Sciences, Microscale Joint Laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P.R. China), Fax: (+86) 551-3606266
    • Hefei National Laboratory for Physical Sciences, Microscale Joint Laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026 (P.R. China), Fax: (+86) 551-3606266

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Abstract

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12-Step program: The combined use of cinchona alkaloid based amine and chiral phosphoric acid enabled the asymmetric alkylation reaction of 3-hydroxyoxindoles with aldehydes to give 3,3′-disubstituted oxindoles in excellent enantioselectivities, which allows for the enantioselective total synthesis of (+)-gliocladin C in 12 steps from 3-hydroxyoxindole with 19 % overall yield (see scheme; PMB=para-methoxybenzyl).

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