# Construction of the Bicyclic Carbon Framework of Euphosalicin

**Authors:** David Schachamayr, Johanna Templ, Matthias Weil, Peter Gaertner, Valentin S. Enev

PMC · DOI: 10.1021/acs.joc.4c01147 · The Journal of Organic Chemistry · 2024-06-27

## TL;DR

This paper describes the synthesis of a complex natural compound called euphosalicin, focusing on constructing its carbon framework.

## Contribution

The paper presents a novel synthetic route to the C11/C12 (Z) isomer of the euphosalicin skeleton.

## Key findings

- Asymmetric dihydroxylations and ring-closing enyne metatheses were successfully applied in the synthesis.
- Highly advanced precursors for macrocyclization studies were isolated.
- The unique C11/C12 (Z) isomer of the euphosalicin skeleton was prepared.

## Abstract

Our studies toward the total synthesis of the natural
product euphosalicin
(1) are presented. Different approaches targeting key
intermediates are described, the synthesis of which includes findings
on asymmetric dihydroxylations and ring-closing enyne metatheses (RCEYM).
Their connection allowed the isolation of highly advanced precursors
for studies on macrocyclizations. Our efforts culminated in the preparation
of the unique C11/C12 (Z) isomer of the C13 nor methyl skeleton of euphosalicin (1).

## Linked entities

- **Chemicals:** euphosalicin (PubChem CID 10259855)

## Full-text entities

- **Chemicals:** Carbon (MESH:D002244), Euphosalicin (-)

## Full text

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## Figures

14 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11267605/full.md

## References

30 references — full list in the complete paper: https://tomesphere.com/paper/PMC11267605/full.md

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Source: https://tomesphere.com/paper/PMC11267605