trans-acetonide controlled endo-selective intramolecular nitrone-alkene cycloaddition of hept-6-enoses: A facile entry to calystegines, tropanes, and hydroxylated aminocycloheptanes

Tony K.M. Shing, Wai F. Wong, Taketo Ikeno, Tohru Yamada

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

(Chemical Equation Presented) High-yielding endo-selective intramolecular nitrone-alkene cycloaddition (INAC) reactions of hept-6-enoses controlled by a trans-acetonide to give bridged bicyclo[4.2.1]isoxazolidines exclusively are realized for the first time. The cycloadducts were readily transformed into calystegine, tropane, and hydroxylated aminocycloheptane frameworks.

Original languageEnglish
Pages (from-to)207-209
Number of pages3
JournalOrganic Letters
Volume9
Issue number2
DOIs
Publication statusPublished - 2007 Jan 18

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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