Asymmetric and highly stereoselective synthesis of the def-ring moiety of (-)-FR182877 and its derivative inducing mitotic arrest

Yu Kobayakawa; Yusuke Mori; Hideki Okajima; Yasuhiko Terada; Masahisa Nakada

doi:10.1021/ol300615w

Asymmetric and highly stereoselective synthesis of the def-ring moiety of (-)-FR182877 and its derivative inducing mitotic arrest

Yu Kobayakawa, Yusuke Mori, Hideki Okajima, Yasuhiko Terada, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

The asymmetric and highly stereoselective synthesis of compound 1, which corresponds exactly to the DEF-ring moiety of (-)-FR182877, and the biological activities of its derivatives are described. All derivatives of 1 showed no activity in the tubulin polymerization assay, but one derivative was shown to have the ability to induce mitotic arrest by interfering with microtubule dynamics, and the cellular effects are similar to those of paclitaxel.

Original language	English
Pages (from-to)	2086-2089
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	8
DOIs	https://doi.org/10.1021/ol300615w
Publication status	Published - 2012 Apr 20

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol300615w

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abstract = "The asymmetric and highly stereoselective synthesis of compound 1, which corresponds exactly to the DEF-ring moiety of (-)-FR182877, and the biological activities of its derivatives are described. All derivatives of 1 showed no activity in the tubulin polymerization assay, but one derivative was shown to have the ability to induce mitotic arrest by interfering with microtubule dynamics, and the cellular effects are similar to those of paclitaxel.",

author = "Yu Kobayakawa and Yusuke Mori and Hideki Okajima and Yasuhiko Terada and Masahisa Nakada",

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AU - Kobayakawa, Yu

AU - Mori, Yusuke

AU - Okajima, Hideki

AU - Terada, Yasuhiko

AU - Nakada, Masahisa

PY - 2012/4/20

Y1 - 2012/4/20

N2 - The asymmetric and highly stereoselective synthesis of compound 1, which corresponds exactly to the DEF-ring moiety of (-)-FR182877, and the biological activities of its derivatives are described. All derivatives of 1 showed no activity in the tubulin polymerization assay, but one derivative was shown to have the ability to induce mitotic arrest by interfering with microtubule dynamics, and the cellular effects are similar to those of paclitaxel.

AB - The asymmetric and highly stereoselective synthesis of compound 1, which corresponds exactly to the DEF-ring moiety of (-)-FR182877, and the biological activities of its derivatives are described. All derivatives of 1 showed no activity in the tubulin polymerization assay, but one derivative was shown to have the ability to induce mitotic arrest by interfering with microtubule dynamics, and the cellular effects are similar to those of paclitaxel.

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Asymmetric and highly stereoselective synthesis of the def-ring moiety of (-)-FR182877 and its derivative inducing mitotic arrest

Abstract

ASJC Scopus subject areas

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