Synthesis of (±)-8-deisopropyladunctin B.
(±)-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.
Kyoto Pharmaceutical University, 5 Misasagi-Nakauchi, Yamashina, Kyoto 607-8414, Japan.
Sayo
S
Nomura
Kenji
K
Arimitsu
Satoshi
S
Yamaguchi
Yuya
Y
Kosuga
Yuko
Y
Kakimoto
Takanori
T
Komai
Kazumasa
K
Hasegawa
Akira
A
Nakanishi
Tamami
T
Miyoshi
Hiroki
H
Iwasaki
Minoru
M
Ozeki
Ikuo
I
Kawasaki
Ai
A
Kurume
Shunsaku
S
Ohta
Masayuki
M
Yamashita
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D003998:Dicarboxylic Acids / Q000737:chemistry; D031701:Piper / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry
C571692:8-deisopropyladunctin B; D001572:Benzofurans; D003998:Dicarboxylic Acids; D011714:Pyrans; D013452:Sulfonium Compounds; C554865:dimethylsulfoxonium methylide; C105430:benzofuran