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

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)7217-7222
Number of pages6
JournalTetrahedron
Volume73
Issue number51
DOIs
Publication statusPublished - 2017 Dec 21

Fingerprint

Spironolactone
Stereochemistry
Skeleton
Scaffolds
undecane
cotylenin A
4-ketoglucose
1,1-dimethoxyethane

Keywords

  • 4-Ketoglucoside
  • Acyl migration
  • Cotylenin A
  • Natural product synthesis
  • Spirolactone
  • Tricyclic bisacetal

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Construction of 2,6,9,11-tetraoxatricyclo[6.2.1.03,8]undecane containing 4-keto-D-glucose skeleton. / Fujitani, Ban; Hanaya, Kengo; Higashibayashi, Shuhei; Shoji, Mitsuru; Sugai, Takeshi.

In: Tetrahedron, Vol. 73, No. 51, 21.12.2017, p. 7217-7222.

Research output: Contribution to journalArticle

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AU - Sugai, Takeshi

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