A concise synthesis of peramine, a metabolite of endophytic fungi

ABSTRACT

The total synthesis of peramine, a natural product isolated from an endophytic fungi, has been achieved in four steps and 34% overall yield from known compounds. The key step was the one-pot construction of the pyrrolopyrazinone ring from pyrrole amide and propargyl bromide. The preparation of peramine-d₄ as an internal standard for quantitative analysis by MS is also described.

Graphical Abstract

Peramine, a natural product isolated from an endophytic fungi, was synthesized in four steps by one-pot construction of the pyrrolopyrazinone ring as a key step.

KEYWORDS:

• Peramine
• pyrrolopyrazinone
• guanidine
• one-pot reaction
• N-propargylation

Acknowledgments

The authors thank Prof. T. Kusumi (Tokyo Institute of Technology) and Mr. K. Koga (Nagoya University) for valuable discussion on ¹³C NMR spectrum of peramine-d₄. Y.Y. thanks to the Program for Leading Graduate Schools: IGER Program in Green Natural Sciences from MEXT.

Disclosure statement

No potential conflict of interest was reported by the authors.

Supplementary material

Supplemental data for this article can be accessed here.

Additional information

Funding

This work was supported by a Grant-in-Aid for Scientific Research (B) (No.16H04915) and Grants-in-Aid for Scientific Research on Innovative Areas [16H04915,18H04400] from MEXT; Japan Society for the Promotion of Science.