Synthetic Studies on Sesquiterpenoids from D-Glucose-Total Syntheses of (+)-Eremantholide A and (-)-Verrucarol-

Ken Ichi Takao, Jun Ishihara, Kin Ichi Tadano

研究成果: Article査読

6 被引用数 (Scopus)

抄録

Enantiospecific total syntheses of (+)-eremantholide A(6) and (-)-verrucarol (41) are described. Both total syntheses began with our enantiopure building block 1, which was prepared from D-glucose. The total synthesis of 6 features (1) regio- and stereoselective radical carbocyclization applied to 16, and (2) nine-membered ring formation by the coupling reaction of the A/B ring equivalent 35 with 3(2H)-furanone 8 followed by a vinylogous aldol reaction applied to 38. The key steps for the total synthesis of 41 are (1) intramolecular Knoevenagel cyclization applied to 48, (2) construction of the consecutive quaternary carbon center by sequential alkylation and aldol reaction applied to γ-lactone 54, and (3) a skeletal rearrangement applied to 68β for the trichothecene ring system construction.

本文言語English
ページ(範囲)1026-1035
ページ数10
ジャーナルYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
56
12
DOI
出版ステータスPublished - 1998

ASJC Scopus subject areas

  • Organic Chemistry

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