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 › peer-review

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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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AU - Ohta, Kazumi

AU - Kano, Takaaki

AU - Nakata, Masaya

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AB - 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.

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A novel monocyclic dienediyne system: Synthesis and mode of aromatization

Abstract

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