# A convergent synthetic approach to the tetracyclic core framework of khayanolide-type limonoids

**Authors:** Zhiyang Zhang, Jialei Hu, Hanfeng Ding, Li Zhang, Peirong Rao

PMC · DOI: 10.3762/bjoc.21.75 · Beilstein Journal of Organic Chemistry · 2025-05-12

## TL;DR

This paper presents a new method to build the complex tetracyclic core of khayanolide-type limonoids in a controlled and efficient way.

## Contribution

The paper introduces a novel convergent synthetic strategy for constructing the tetracyclic core of khayanolide-type limonoids with enantioselectivity.

## Key findings

- The method uses acylative kinetic resolution of a benzylic alcohol as a key step.
- A 1,2-Grignard addition and an AcOH-interrupted Nazarov cyclization complete the tetracyclic core formation.
- The approach provides an advanced intermediate with high stereochemical control.

## Abstract

A convergent approach for the enantioselective construction of an advanced intermediate containing the [5,5,6,6]-tetracyclic core framework of the khayanolide-type limonoids was described. The strategy features an acylative kinetic resolution of the benzylic alcohol, a 1,2-Grignard addition and an AcOH-interrupted Nazarov cyclization.

## Linked entities

- **Chemicals:** AcOH (PubChem CID 176)

## Full-text entities

- **Chemicals:** benzylic alcohol (MESH:D019905), AcOH (-), limonoids (MESH:D036701)

## Full text

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## Figures

5 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12117208/full.md

## References

48 references — full list in the complete paper: https://tomesphere.com/paper/PMC12117208/full.md

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Source: https://tomesphere.com/paper/PMC12117208