# Rapid access to the core of malayamycin A by intramolecular dipolar cycloaddition

**Authors:** Yilin Liu, Yuchen Yang, Chen Yang, Sha-Hua Huang, Jian Jin, Ran Hong

PMC · DOI: 10.3762/bjoc.21.196 · Beilstein Journal of Organic Chemistry · 2025-11-17

## TL;DR

A new chemical method efficiently builds the core structure of malayamycin A and similar compounds, which could lead to better fungicides.

## Contribution

A streamlined, alkene-free approach using intramolecular dipolar cycloaddition to access the core of malayamycin A and related uracil nucleosides.

## Key findings

- The oxazoline-based latent functionality strategy successfully unmasked the 1,2-hydroxyamine moiety.
- The method avoids alkene functionalization, simplifying prior synthetic routes.
- The approach enables the synthesis of diverse uracil nucleosides and derivatives for fungicide development.

## Abstract

We have streamlined a dipolar cycloaddition approach to assemble the core of malayamycin A and other related uracil nucleosides possessing the common bicyclic perhydrofuropyran framework. The latent functionality strategy employing oxazoline to unmask the 1,2-hydroxyamine moiety proves feasible, eliminating the need for alkene functionalization required in previous endeavours. This current strategy provides a reliable platform for accessing diverse uracil nucleosides and their derivatives, facilitating the development of potent fungicides.

## Linked entities

- **Chemicals:** malayamycin A (PubChem CID 9819404), oxazoline (PubChem CID 68157)

## Full-text entities

- **Chemicals:** 1,2-hydroxyamine (-), alkene (MESH:D000475), malayamycin A (MESH:C493874)

## Full text

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## Figures

6 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12642950/full.md

## References

41 references — full list in the complete paper: https://tomesphere.com/paper/PMC12642950/full.md

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Source: https://tomesphere.com/paper/PMC12642950