Synthesis of (±)-8-Deisopropyladunctin B

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...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 2012/01/01, Vol.60(1), pp.94-103
Hauptverfasser: 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
Format: Artikel
Sprache:eng
Schlagworte:
8-deisopropyladunctin B
adunctin B
Benzofurans - chemical synthesis
Benzofurans - chemistry
Dicarboxylic Acids - chemistry
Piper - chemistry
Plant Leaves - chemistry
Pyrans - chemical synthesis
Pyrans - chemistry
skeleton transformation
Stereoisomerism
Sulfonium Compounds - chemistry
total synthesis
ylide
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Beschreibung
Zusammenfassung:(±)-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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.60.94