Synthesis of (±)-8-deisopropyladunctin B.

作者信息

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

机构信息

Kyoto Pharmaceutical University, 5 Misasagi-Nakauchi, Yamashina, Kyoto 607-8414, Japan.

出版信息

Chem Pharm Bull (Tokyo). 2012;60(1):94-103. doi: 10.1248/cpb.60.94.

(±)-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.