# Asymmetric Total Synthesis and Structural Reassignment of Nervione

**Authors:** Kunita Phakdeeyothin, Jian-Liang Li, Yi-Tian Hong, Rong-Jie Chein

PMC · DOI: 10.1021/acs.joc.5c00258 · 2025-03-19

## TL;DR

This paper describes the complete synthesis of a natural compound called nervione and corrects its molecular structure based on new evidence.

## Contribution

The paper provides the first asymmetric total synthesis of nervione and corrects its absolute configuration.

## Key findings

- Nervione was synthesized in 10 steps from resorcinol using ortho-directed strategies and a key diastereoselective reduction.
- Circular dichroism (CD) spectra discrepancies led to the reassignment of nervione’s absolute configuration to (3R, 8S).

## Abstract

We report the asymmetric
total synthesis of optically active nervione
in both (+) and (−) forms, a natural product initially isolated
from Nervilia concolor in 2022. Beginning
with commercially available resorcinol, optically pure nervione was
synthesized in 10 steps, employing a combination of ortho-directed strategies and a crucial late-stage, Lewis acid-mediated,
highly diastereoselective reduction. Discrepancies observed in circular
dichroism (CD) spectra prompted the reassignment of nervione’s
absolute configuration from (3S, 8R) to (3R, 8S).

## Linked entities

- **Chemicals:** resorcinol (PubChem CID 5054)
- **Species:** Nervilia concolor (taxon 2806780)

## Full-text entities

- **Chemicals:** resorcinol (MESH:C031389), (3S, 8R (-), Lewis acid (MESH:D058116)
- **Species:** Nervilia concolor (species) [taxon 2806780]

## Figures

10 figures with captions in the complete paper: https://tomesphere.com/paper/PMC11959527/full.md

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Source: https://tomesphere.com/paper/PMC11959527