Total synthesis of terfestatins a and B

Shun Sugawara; Yasuhiro Meguro; Shuntaro Sato; Masaru Enomoto; Yusuke Ogura; Shigefumi Kuwahara

doi:10.1016/j.tetlet.2020.151891

Total synthesis of terfestatins a and B

Shun Sugawara, Yasuhiro Meguro, Shuntaro Sato, Masaru Enomoto, Yusuke Ogura, Shigefumi Kuwahara

AGR - Bioscience and Biotechnology for Future Bioindustries

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

Abstract

Terfestatin A, a specific inhibitor of auxin signaling, has been synthesized from a known aromatic aldehyde in 21% overall yield via five steps. The first total synthesis of terfestatin B with potent neuroprotective activity has also been accomplished in eight steps from the same aromatic aldehyde in 30% overall yield through a common intermediate. The key feature of this synthesis is the utilization of the aldehyde functionality of the starting material both as a directing group for regioselective O-protection and as a masked hydroxy group.

Original language	English
Article number	151891
Journal	Tetrahedron Letters
Volume	61
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2020.151891
Publication status	Published - 2020 May 21

Keywords

DWAQMWPHCVWJMI-SMTRDTIPSA-N
Natural product
Terfestatin
Total synthesis
UTRHHGVQLUCOIT-NZXWXYQFSA-N
p-Terphenyl

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2020.151891

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title = "Total synthesis of terfestatins a and B",

abstract = "Terfestatin A, a specific inhibitor of auxin signaling, has been synthesized from a known aromatic aldehyde in 21% overall yield via five steps. The first total synthesis of terfestatin B with potent neuroprotective activity has also been accomplished in eight steps from the same aromatic aldehyde in 30% overall yield through a common intermediate. The key feature of this synthesis is the utilization of the aldehyde functionality of the starting material both as a directing group for regioselective O-protection and as a masked hydroxy group.",

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T1 - Total synthesis of terfestatins a and B

AU - Sugawara, Shun

AU - Meguro, Yasuhiro

AU - Sato, Shuntaro

AU - Enomoto, Masaru

AU - Ogura, Yusuke

AU - Kuwahara, Shigefumi

PY - 2020/5/21

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N2 - Terfestatin A, a specific inhibitor of auxin signaling, has been synthesized from a known aromatic aldehyde in 21% overall yield via five steps. The first total synthesis of terfestatin B with potent neuroprotective activity has also been accomplished in eight steps from the same aromatic aldehyde in 30% overall yield through a common intermediate. The key feature of this synthesis is the utilization of the aldehyde functionality of the starting material both as a directing group for regioselective O-protection and as a masked hydroxy group.

AB - Terfestatin A, a specific inhibitor of auxin signaling, has been synthesized from a known aromatic aldehyde in 21% overall yield via five steps. The first total synthesis of terfestatin B with potent neuroprotective activity has also been accomplished in eight steps from the same aromatic aldehyde in 30% overall yield through a common intermediate. The key feature of this synthesis is the utilization of the aldehyde functionality of the starting material both as a directing group for regioselective O-protection and as a masked hydroxy group.

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KW - p-Terphenyl

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Total synthesis of terfestatins a and B

Abstract

Keywords

ASJC Scopus subject areas

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