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

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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.

Graphical abstract: Total synthesis of exigurin: the Ugi reaction in a hypothetical biosynthesis of natural products

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Article information


Submitted
17 Oct 2019
Accepted
10 Dec 2019
First published
11 Dec 2019

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

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

S. Hosokawa, K. Nakanishi, Y. Udagawa, M. Maeda, S. Sato, K. Nakano, T. Masuda and Y. Ichikawa, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02249J

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