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

^*Corresponding author for this work

School of Advanced Science and Engineering

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

17 Citations (Scopus)

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.

Original language	English
Pages (from-to)	687-693
Number of pages	7
Journal	Organic and Biomolecular Chemistry
Volume	18
Issue number	4
DOIs	https://doi.org/10.1039/c9ob02249j
Publication status	Published - 2020

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/c9ob02249j

Cite this

@article{265e2d4616114d909072305323045029,

title = "Total synthesis of exigurin: The Ugi reaction in a hypothetical biosynthesis of natural products",

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",

note = "Publisher Copyright: This journal is {\textcopyright} The Royal Society of Chemistry.",

year = "2020",

doi = "10.1039/c9ob02249j",

language = "English",

volume = "18",

pages = "687--693",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "4",

}

TY - JOUR

T1 - Total synthesis of exigurin

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

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/85078685138

UR - https://www.scopus.com/pages/publications/85078685138#tab=citedBy

U2 - 10.1039/c9ob02249j

DO - 10.1039/c9ob02249j

M3 - Article

C2 - 31903473

AN - SCOPUS:85078685138

SN - 1477-0520

VL - 18

SP - 687

EP - 693

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 4

ER -

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

Abstract

UN SDGs

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this