Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B

Takanori Matsumaru; Toshiaki Sunazuka; Tomoyasu Hirose; Aki Ishiyama; Miyuki Namatame; Takashi Fukuda; Hiroshi Tomoda; Kazuhiko Otoguro; Satoshi Omura

doi:10.1016/j.tet.2008.05.035

Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B

Takanori Matsumaru, Toshiaki Sunazuka, Tomoyasu Hirose, Aki Ishiyama, Miyuki Namatame, Takashi Fukuda, Hiroshi Tomoda, Kazuhiko Otoguro, Satoshi Omura

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

8 Citations (Scopus)

Abstract

The first, concise total synthesis of (±)-tensyuic acids B, C, and E, using chemoselective formal S_N2′ type Grignard reactions and selective esterification, is described. In addition, the optical purity of natural (±)-tensyuic acid B was determined using Chirabite-AR. Synthetic tensyuic acids, together with their intermediate compounds, were found to possess useful bioactive properties, with some of them showing potent activity against Trypanosoma brucei brucei strain GUTat 3.1.

Original language	English
Pages (from-to)	7369-7377
Number of pages	9
Journal	Tetrahedron
Volume	64
Issue number	30-31
DOIs	https://doi.org/10.1016/j.tet.2008.05.035
Publication status	Published - 2008 Jul 21
Externally published	Yes

Keywords

Anti-trypanosomal activity
Chirabite-AR
Formal S2 reaction
Selective esterification
Tensyic acid
Total synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2008.05.035

Cite this

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title = "Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B",

abstract = "The first, concise total synthesis of (±)-tensyuic acids B, C, and E, using chemoselective formal SN2′ type Grignard reactions and selective esterification, is described. In addition, the optical purity of natural (±)-tensyuic acid B was determined using Chirabite-AR. Synthetic tensyuic acids, together with their intermediate compounds, were found to possess useful bioactive properties, with some of them showing potent activity against Trypanosoma brucei brucei strain GUTat 3.1.",

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doi = "10.1016/j.tet.2008.05.035",

language = "English",

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TY - JOUR

T1 - Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B

AU - Matsumaru, Takanori

AU - Sunazuka, Toshiaki

AU - Hirose, Tomoyasu

AU - Ishiyama, Aki

AU - Namatame, Miyuki

AU - Fukuda, Takashi

AU - Tomoda, Hiroshi

AU - Otoguro, Kazuhiko

AU - Omura, Satoshi

PY - 2008/7/21

Y1 - 2008/7/21

N2 - The first, concise total synthesis of (±)-tensyuic acids B, C, and E, using chemoselective formal SN2′ type Grignard reactions and selective esterification, is described. In addition, the optical purity of natural (±)-tensyuic acid B was determined using Chirabite-AR. Synthetic tensyuic acids, together with their intermediate compounds, were found to possess useful bioactive properties, with some of them showing potent activity against Trypanosoma brucei brucei strain GUTat 3.1.

AB - The first, concise total synthesis of (±)-tensyuic acids B, C, and E, using chemoselective formal SN2′ type Grignard reactions and selective esterification, is described. In addition, the optical purity of natural (±)-tensyuic acid B was determined using Chirabite-AR. Synthetic tensyuic acids, together with their intermediate compounds, were found to possess useful bioactive properties, with some of them showing potent activity against Trypanosoma brucei brucei strain GUTat 3.1.

KW - Anti-trypanosomal activity

KW - Chirabite-AR

KW - Formal S2 reaction

KW - Selective esterification

KW - Tensyic acid

KW - Total synthesis

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DO - 10.1016/j.tet.2008.05.035

M3 - Article

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SN - 0040-4020

VL - 64

SP - 7369

EP - 7377

JO - Tetrahedron

JF - Tetrahedron

IS - 30-31

ER -

Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B

Abstract

Keywords

ASJC Scopus subject areas

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