Total synthesis of (±)-trachyspic acid and determination of the relative configuration

Kanako Hirai; Hidenori Ooi; Tomoyuki Esumi; Yoshiharu Iwabuchi; Susumi Hatakeyama

doi:10.1021/ol0275264

Total synthesis of (±)-trachyspic acid and determination of the relative configuration

Kanako Hirai, Hidenori Ooi, Tomoyuki Esumi, Yoshiharu Iwabuchi, Susumi Hatakeyama

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

38 Citations (Scopus)

Abstract

The first total synthesis of (±)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished based on Cr(II)/Ni(II)-mediated reaction of the aldehyde containing the citric acid moiety and the long-chain triflate, and the relative configuration of this natural product was determined.

Original language	English
Pages (from-to)	857-859
Number of pages	3
Journal	Organic letters
Volume	5
Issue number	6
DOIs	https://doi.org/10.1021/ol0275264
Publication status	Published - 2003 Mar 20
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0275264

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title = "Total synthesis of (±)-trachyspic acid and determination of the relative configuration",

abstract = "The first total synthesis of (±)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished based on Cr(II)/Ni(II)-mediated reaction of the aldehyde containing the citric acid moiety and the long-chain triflate, and the relative configuration of this natural product was determined.",

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AU - Ooi, Hidenori

AU - Esumi, Tomoyuki

AU - Iwabuchi, Yoshiharu

AU - Hatakeyama, Susumi

PY - 2003/3/20

Y1 - 2003/3/20

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AB - The first total synthesis of (±)-trachyspic acid, a tumor cell heparanase inhibitor, was accomplished based on Cr(II)/Ni(II)-mediated reaction of the aldehyde containing the citric acid moiety and the long-chain triflate, and the relative configuration of this natural product was determined.

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M3 - Article

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Total synthesis of (±)-trachyspic acid and determination of the relative configuration

Abstract

ASJC Scopus subject areas

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