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

Kenichi Takao, Jun Ishihara, Kin Ichi Tadano

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1026-1035
Number of pages10
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume56
Issue number12
Publication statusPublished - 1998

Fingerprint

Glucose
Trichothecenes
Cyclization
Alkylation
Lactones
Carbon
verrucarol
eremantholide A
3-hydroxybutanal

Keywords

  • (+)-eremantholide A
  • (-)-verrucarol
  • Consecutive quaternary carbon center
  • D-glucose
  • Enantiopure building block
  • Enantiospecific total synthesis
  • Intramolecular Knoevenagel cyclization
  • Nine-membered ring formation
  • Radical carbocyclization

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthetic Studies on Sesquiterpenoids from D-Glucose-Total Syntheses of (+)-Eremantholide A and (-)-Verrucarol-. / Takao, Kenichi; Ishihara, Jun; Tadano, Kin Ichi.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 56, No. 12, 1998, p. 1026-1035.

Research output: Contribution to journalArticle

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