Synthesis of (±)-8-Deisopropyladunctin B

Sayo Nomura; Kenji Arimitsu; Satoshi Yamaguchi; Yuya Kosuga; Yuko Kakimoto; Takanori Komai; Kazumasa Hasegawa; Akira Nakanishi; Tamami Miyoshi; Hiroki Iwasaki; Minoru Ozeki; Ikuo Kawasaki; Ai Kurume; Shunsaku Ohta; Masayuki Yamashita

doi:10.1248/cpb.60.94

Regular Articles

Synthesis of (±)-8-Deisopropyladunctin B

Sayo Nomura, Kenji Arimitsu, Satoshi Yamaguchi, Yuya Kosuga, Yuko Kakimoto, Takanori Komai, Kazumasa Hasegawa, Akira Nakanishi, Tamami Miyoshi, Hiroki Iwasaki, Minoru Ozeki, Ikuo Kawasaki, Ai Kurume, Shunsaku Ohta, Masayuki Yamashita

Author information

Keywords: adunctin B, 8-deisopropyladunctin B, total synthesis, ylide, skeleton transformation

JOURNAL FREE ACCESS

2012 Volume 60 Issue 1 Pages 94-103

DOI https://doi.org/10.1248/cpb.60.94

Details

Abstract

(±)-8-Deisopropyladunctin B, the deisopropyl form of adunctin B, which was isolated from the leaves of Piper aduncum (Piperaceae) collected in Papua New Guinea, was synthesized in 0.77% overall yield in 17 steps from 5,7-dimethoxycoumarin-3-carboxylate. The key step was our original stereoconvergent skeleton transformation from 1,2,2a,8b-tetrahydro-3H-benzo[b]cyclobuta[d]pyran-3-one to 1,2,4a,9b-tetrahydrodibenzofuran-4-ol with dimethylsulfoxonium methylide.

Corresponding author

Register with J-STAGE for free!