A novel monocyclic dienediyne system: Synthesis and mode of aromatization

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

Research output: Contribution to journalArticle

15 Citations (Scopus)

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

Fingerprint

Xylitol
Aromatization
Sulfhydryl Compounds
Aldehydes
Condensation
neocarzinostatin chromophore
3-hydroxybutanal
Ring Chromosome 14 Syndrome

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A novel monocyclic dienediyne system : Synthesis and mode of aromatization. / Toshima, Kazunobu; Yanagawa, Koji; Ohta, Kazumi; Kano, Takaaki; Nakata, Masaya.

In: Tetrahedron Letters, Vol. 35, No. 10, 07.03.1994, p. 1573-1576.

Research output: Contribution to journalArticle

Toshima, Kazunobu ; Yanagawa, Koji ; Ohta, Kazumi ; Kano, Takaaki ; Nakata, Masaya. / A novel monocyclic dienediyne system : Synthesis and mode of aromatization. In: Tetrahedron Letters. 1994 ; Vol. 35, No. 10. pp. 1573-1576.
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