Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol

Teruhiko Ishikawa, Yoshihiro Shimizu, Takayuki Kudoh, Seiki Saito

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

(Matrix presented). A diastereoisomeric mixture of 1-nitro-6-heptene-2,3,4, 5-tetraol derivative (A) was prepared by Henry reaction between D-glucose-based aldehyde and nitromethane. Only the (2S)-isomer of A led to cyclitol (B) via nitronate-olefin cycloaddition on treatment with TMS-CI and Et3N in the presence of catalytic DMAP followed by acid treatment. (+)-Cyclophellitol (1) was synthesized from B in eight steps.

Original languageEnglish
Pages (from-to)3879-3882
Number of pages4
JournalOrganic Letters
Volume5
Issue number21
DOIs
Publication statusPublished - Oct 16 2003

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Conversion of D-Glucose to Cyclitol with Hydroxymethyl Substituent via Intramolecular Silyl Nitronate Cycloaddition Reaction: Application to Total Synthesis of (+)-Cyclophellitol'. Together they form a unique fingerprint.

  • Cite this