Total synthesis of exigurin: The Ugi reaction in a hypothetical biosynthesis of natural products

Seijiro Hosokawa; Keisuke Nakanishi; Yutaro Udagawa; Mitsutoshi Maeda; Seiya Sato; Keiji Nakano; Toshiya Masuda; Yoshiyasu Ichikawa

doi:10.1039/c9ob02249j

Total synthesis of exigurin: The Ugi reaction in a hypothetical biosynthesis of natural products

Seijiro Hosokawa^*, Keisuke Nakanishi, Yutaro Udagawa, Mitsutoshi Maeda, Seiya Sato, Keiji Nakano, Toshiya Masuda, Yoshiyasu Ichikawa

^*この研究の対応する著者

先進理工学部

研究成果: Article › 査読

13 被引用数 (Scopus)

抄録

The first total synthesis of a marine natural product, exigurin, has been accomplished in 13 steps starting from (+)-menthone. The key intermediate (-)-10-epi-axisonitrile-3 was prepared by stereoselective intramolecular cyclopropanation followed by a cyclopropane ring opening reaction by the azide anion. The bioinspired Ugi reaction of (-)-10-epi-axisonitrile-3, formaldehyde, sarcosine and methanol successfully constructed the target exigurin in which its terpene and amino acid units were linked through an amide bond.

本文言語	English
ページ（範囲）	687-693
ページ数	7
ジャーナル	Organic and Biomolecular Chemistry
巻	18
号	4
DOI	https://doi.org/10.1039/c9ob02249j
出版ステータス	Published - 2020

ASJC Scopus subject areas

生化学
物理化学および理論化学
有機化学

UN SDG

この成果は、次の持続可能な開発目標に貢献しています

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10.1039/c9ob02249j

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abstract = "The first total synthesis of a marine natural product, exigurin, has been accomplished in 13 steps starting from (+)-menthone. The key intermediate (-)-10-epi-axisonitrile-3 was prepared by stereoselective intramolecular cyclopropanation followed by a cyclopropane ring opening reaction by the azide anion. The bioinspired Ugi reaction of (-)-10-epi-axisonitrile-3, formaldehyde, sarcosine and methanol successfully constructed the target exigurin in which its terpene and amino acid units were linked through an amide bond.",

author = "Seijiro Hosokawa and Keisuke Nakanishi and Yutaro Udagawa and Mitsutoshi Maeda and Seiya Sato and Keiji Nakano and Toshiya Masuda and Yoshiyasu Ichikawa",

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doi = "10.1039/c9ob02249j",

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T2 - The Ugi reaction in a hypothetical biosynthesis of natural products

AU - Hosokawa, Seijiro

AU - Nakanishi, Keisuke

AU - Udagawa, Yutaro

AU - Maeda, Mitsutoshi

AU - Sato, Seiya

AU - Nakano, Keiji

AU - Masuda, Toshiya

AU - Ichikawa, Yoshiyasu

PY - 2020

Y1 - 2020

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AB - The first total synthesis of a marine natural product, exigurin, has been accomplished in 13 steps starting from (+)-menthone. The key intermediate (-)-10-epi-axisonitrile-3 was prepared by stereoselective intramolecular cyclopropanation followed by a cyclopropane ring opening reaction by the azide anion. The bioinspired Ugi reaction of (-)-10-epi-axisonitrile-3, formaldehyde, sarcosine and methanol successfully constructed the target exigurin in which its terpene and amino acid units were linked through an amide bond.

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Total synthesis of exigurin: The Ugi reaction in a hypothetical biosynthesis of natural products

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ASJC Scopus subject areas

UN SDG

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