A novel monocyclic dienediyne system: Synthesis and mode of aromatization

Kazunobu Toshima, Koji Yanagawa, Kazumi Ohta, Takaaki Kano, Masaya Nakata

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Abstract

The novel monocyclic dienediyne 2, which is a simplified analogue of the neocarzinostatin chromophore (1), was synthesized from D-xylitol via conversion of the keto-aldehyde 13 into the highly strained 10-membered ring compound 14 by a simple intramolecular aldol condensation as the key step. The mode of cycloaromatization of 2 by a thiol addition, reminiscent of the chemistry of 1, was also demonstrated.

Original languageEnglish
Pages (from-to)1573-1576
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number10
DOIs
Publication statusPublished - 1994 Mar 7

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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