Synthesis of an insecticidal tetrahydroisocoumarin, (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one |
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| Authors: | Kanako Uchida Hidenori Watanabe |
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| Institution: | a Department of Applied Biological Chemistry, Graduate School of Agricultural and Life Sciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-8657, Japan
b Laboratory of Natural Product Chemistry, Center for Basic Research, The Kitasato Institute, 5-9-1 Shi rokane, Minato-ku, Tokyo 108-8642, Japan |
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| Abstract: | The insecticidal tetrahydroisocoumarin, (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one, was synthesized as a racemate and as an optically active form using one-pot esterification-Michael addition-aldol reaction of δ-hydroxy-α,β-unsaturated aldehyde and diketene as a key step. |
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