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Communication | Regular issue | Vol 53, No. 3, 2000, pp.539-542
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8808
Synthesis of (±)-(3R*, 4S*, 4aR*)- 4,8-Dihydoxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one

Kanako Uchida, Hidenori Watanabe, and Takeshi Kitahara*

*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

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 using one-pot esterification—Michael addition—aldol reaction of δ-hydroxy-α,β-unsaturated aldehyde and diketene as a key step.