A novel monocyclic dienediyne system: Synthesis and mode of aromatization

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

doi:10.1016/S0040-4039(00)76761-X

A novel monocyclic dienediyne system: Synthesis and mode of aromatization

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

Department of Applied Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1573-1576
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4039(00)76761-X
Publication status	Published - 1994 Mar 7

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ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Toshima, K., Yanagawa, K., Ohta, K., Kano, T., & Nakata, M. (1994). A novel monocyclic dienediyne system: Synthesis and mode of aromatization. Tetrahedron Letters, 35(10), 1573-1576. https://doi.org/10.1016/S0040-4039(00)76761-X

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10.1016/S0040-4039(00)76761-X