A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A

Yusuke Iijima; Asami Munakata; Kazuo Shin-ya; A. Ganesan; Takayuki Doi; Takashi Takahashi

doi:10.1016/j.tetlet.2009.04.005

A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A

Yusuke Iijima, Asami Munakata, Kazuo Shin-ya, A. Ganesan, Takayuki Doi, Takashi Takahashi

School of Pharmacy

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

25 Citations (Scopus)

Abstract

Spiruchostatin A, a potent histone deacetylase inhibitor, was efficiently synthesized from (3S,4R)-4-amino-3-hydroxy-5-methylhexanoic acid utilizing solid-phase peptide elongation with d-cysteine, d-alanine, and (E)-3-hydroxy-7-thio-4-heptenoic acid and solution-phase macrolactonization, followed by intramolecular disulfide formation.

Original language	English
Pages (from-to)	2970-2972
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2009.04.005
Publication status	Published - 17 Jun 2009

Access to Document

10.1016/j.tetlet.2009.04.005

Cite this

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title = "A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A",

abstract = "Spiruchostatin A, a potent histone deacetylase inhibitor, was efficiently synthesized from (3S,4R)-4-amino-3-hydroxy-5-methylhexanoic acid utilizing solid-phase peptide elongation with d-cysteine, d-alanine, and (E)-3-hydroxy-7-thio-4-heptenoic acid and solution-phase macrolactonization, followed by intramolecular disulfide formation.",

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

year = "2009",

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day = "17",

doi = "10.1016/j.tetlet.2009.04.005",

language = "English",

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journal = "Tetrahedron Letters",

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T1 - A solid-phase total synthesis of the cyclic depsipeptide HDAC inhibitor spiruchostatin A

AU - Iijima, Yusuke

AU - Munakata, Asami

AU - Shin-ya, Kazuo

AU - Ganesan, A.

AU - Doi, Takayuki

AU - Takahashi, Takashi

PY - 2009/6/17

Y1 - 2009/6/17

N2 - Spiruchostatin A, a potent histone deacetylase inhibitor, was efficiently synthesized from (3S,4R)-4-amino-3-hydroxy-5-methylhexanoic acid utilizing solid-phase peptide elongation with d-cysteine, d-alanine, and (E)-3-hydroxy-7-thio-4-heptenoic acid and solution-phase macrolactonization, followed by intramolecular disulfide formation.

AB - Spiruchostatin A, a potent histone deacetylase inhibitor, was efficiently synthesized from (3S,4R)-4-amino-3-hydroxy-5-methylhexanoic acid utilizing solid-phase peptide elongation with d-cysteine, d-alanine, and (E)-3-hydroxy-7-thio-4-heptenoic acid and solution-phase macrolactonization, followed by intramolecular disulfide formation.

U2 - 10.1016/j.tetlet.2009.04.005

DO - 10.1016/j.tetlet.2009.04.005

M3 - Article

VL - 50

SP - 2970

EP - 2972

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 24

ER -