Construction of 2,6,9,11-tetraoxatricyclo[6.2.1.03,8]undecane containing 4-keto-D-glucose skeleton

Ban Fujitani, Kengo Hanaya, Shuhei Higashibayashi, Mitsuru Shoji, Takeshi Sugai

研究成果: Article査読

1 被引用数 (Scopus)

抄録

A unique tricyclic bisacetal, 2,6,9,11-tetraoxatricyclo[6.2.1.03,8]undecane observed in cotylenin A, was constructed in a simplified model compound, based on 6-O-methyl-4-keto-D-glucose as the scaffold to control of the stereochemistry. The key compound was an unprecedented spirolactone formed from the α-(α′-hydroxy)acyloxy dimethyl acetal, accompanied with stereoselective migration of an acyl group. Subsequent intramolecular acetalization between the hydroxy group at the C-3 and the C-1′ hemiacetal position furnished the desired tricyclic bisacetal.

本文言語English
ページ(範囲)7217-7222
ページ数6
ジャーナルTetrahedron
73
51
DOI
出版ステータスPublished - 2017 12 21

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

フィンガープリント 「Construction of 2,6,9,11-tetraoxatricyclo[6.2.1.0<sup>3,8</sup>]undecane containing 4-keto-D-glucose skeleton」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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