# Stereoselective synthesis of an advanced trans-decalin intermediate towards the total synthesis of anthracimycin

**Authors:** Laksamee Jeanmard, Giacomo Lodovici, Ian George, Joshua T. W. Bray, Adrian C. Whitwood, Gavin H. Thomas, Ian J. S. Fairlamb, William P. Unsworth, Paul A. Clarke

PMC · DOI: 10.1039/d4cc01738b · Chemical Communications (Cambridge, England) · 2024-05-07

## TL;DR

This paper presents a new method for making a key part of the anthracimycin molecule using a stereoselective chemical process.

## Contribution

A novel intermolecular Diels–Alder strategy followed by epimerisation to form a trans-decalin framework with precise stereochemistry.

## Key findings

- A stereoselective synthesis of a tricyclic lactone intermediate was achieved.
- The method forms five contiguous sterogenic centres with correct relative and absolute stereochemistry.
- The approach provides an advanced intermediate for the total synthesis of anthracimycin.

## Abstract

Progress towards the total synthesis of the macrolide natural product anthracimycin is described. This new approach utilises an intermolecular Diels–Alder strategy followed by epimeirsation to form the key trans-decalin framework. The route culminates in the stereoselective synthesis of an advanced tricyclic lactone intermediate, containing five contiguous sterogenic centres with the correct relative and absolute stereochemistry required for the anthracimycin core motif.

A stereoselective synthesis of an advanced trans-decalin intermediate towards the total synthesis of anthracimycin is described.

## Linked entities

- **Chemicals:** anthracimycin (PubChem CID 102496082)

## Full text

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## Figures

7 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11131352/full.md

## References

19 references — full list in the complete paper: https://tomesphere.com/paper/PMC11131352/full.md

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Source: https://tomesphere.com/paper/PMC11131352