# Synthesis of the Tetracyclic Core of the Daphlongeranines

**Authors:** Benjamin D. A. Shennan, Peter W. Smith, Yusuke Ogura, Eddy A. Källström, Moses Moustakim, Tudor Balan, Darren J. Dixon

PMC · DOI: 10.1021/acs.orglett.5c03362 · Organic Letters · 2025-10-07

## TL;DR

This paper describes the first successful synthesis of the tetracyclic core of the daphlongeranine natural product family.

## Contribution

The paper introduces a new intramolecular Pd-catalyzed cyclization reaction and an enantioselective synthesis method.

## Key findings

- An 11-step synthetic route was developed for the tetracyclic core.
- A spirocyclization strategy and XAT-initiated Giese addition were successfully applied.
- An enantioselective synthesis of the bicyclic core was demonstrated.

## Abstract

The first synthesis
of the tetracyclic core of the daphlongeranine
natural product family is reported. Containing a tricyclic core unique
to this subfamily of the Daphniphyllum alkaloids
and featuring two quaternary carbons, this 11-step synthetic route
featured the application of a three-step spirocyclization strategy
and development of a new intramolecular Pd-catalyzed cyclization reaction.
Additionally, the route included the application of an XAT-initiated
Giese addition and demonstration of an enantioselective synthesis
of the bicyclic core.

## Full-text entities

- **Chemicals:** carbons (MESH:D002244), Pd (MESH:D010165), Daphlongeranines (-)

## Full text

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## Figures

7 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12538578/full.md

## References

59 references — full list in the complete paper: https://tomesphere.com/paper/PMC12538578/full.md

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Source: https://tomesphere.com/paper/PMC12538578