# Biomimetic Total Synthesis of (±)-Lappaceolides A and B

**Authors:** Rajanish R. Pallerla, Jenna Hakola, Leevi Härkönen, Juha H. Siitonen

PMC · DOI: 10.1021/acs.orglett.5c02445 · 2025-10-01

## TL;DR

Scientists synthesized lappaceolides A and B in two steps using a biomimetic reaction, supporting their origin from a natural compound.

## Contribution

A novel two-step total synthesis of lappaceolides A and B using a biomimetic domino reaction.

## Key findings

- The synthesis used a vinylogous-Michael–oxa-Michael domino reaction with Cs2CO3 in 1,2-DCE.
- The reaction required elevated temperatures and precise kinetic control.
- The synthesis supports the hypothesis that lappaceolides are dimers of siphonodin.

## Abstract

The first total synthesis of lappaceolides A and B is
achieved
in two steps by using a biomimetic vinylogous-Michael–oxa-Michael
domino reaction. The domino reaction proceeds with Cs2CO3 in 1,2-DCE at elevated temperatures and requires careful
kinetic control. The total synthesis provides further proof of the
biosynthetic hypothesis of lappaceolides being dimers of the natural
product siphonodin.

## Linked entities

- **Chemicals:** Cs2CO3 (PubChem CID 10796), 1,2-DCE (PubChem CID 11)

## Full-text entities

- **Chemicals:** (+-)-Lappaceolides A and B. (-)

## Figures

4 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12519463/full.md

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Source: https://tomesphere.com/paper/PMC12519463