A total synthesis of spiruchostatin A

Takayuki Doi; Yusuke Iijima; Kazuo Shin-Ya; A. Ganesan; Takashi Takahashi

doi:10.1016/j.tetlet.2005.12.031

A total synthesis of spiruchostatin A

Takayuki Doi, Yusuke Iijima, Kazuo Shin-Ya, A. Ganesan, Takashi Takahashi

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

60 Citations (Scopus)

Abstract

We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization using the Shiina method.

Original language	English
Pages (from-to)	1177-1180
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	7
DOIs	https://doi.org/10.1016/j.tetlet.2005.12.031
Publication status	Published - 2006 Feb 13
Externally published	Yes

Keywords

Asymmetric aldol reaction
Cyclic depsipeptide
Natural product synthesis
Spiruchostatin

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.12.031

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title = "A total synthesis of spiruchostatin A",

abstract = "We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization using the Shiina method.",

keywords = "Asymmetric aldol reaction, Cyclic depsipeptide, Natural product synthesis, Spiruchostatin",

author = "Takayuki Doi and Yusuke Iijima and Kazuo Shin-Ya and A. Ganesan and Takashi Takahashi",

note = "Funding Information: This work was supported by a Grant-In-Aid from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 16350051).",

year = "2006",

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doi = "10.1016/j.tetlet.2005.12.031",

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T1 - A total synthesis of spiruchostatin A

AU - Doi, Takayuki

AU - Iijima, Yusuke

AU - Shin-Ya, Kazuo

AU - Ganesan, A.

AU - Takahashi, Takashi

N1 - Funding Information: This work was supported by a Grant-In-Aid from the Ministry of Education, Culture, Sports, Science and Technology, Japan (No. 16350051).

PY - 2006/2/13

Y1 - 2006/2/13

N2 - We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization using the Shiina method.

AB - We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization using the Shiina method.

KW - Asymmetric aldol reaction

KW - Cyclic depsipeptide

KW - Natural product synthesis

KW - Spiruchostatin

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DO - 10.1016/j.tetlet.2005.12.031

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SP - 1177

EP - 1180

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 7

ER -

A total synthesis of spiruchostatin A

Abstract

Keywords

ASJC Scopus subject areas

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