Biomimetic Total Synthesis of Dispirocochlearoids A–C and Related <i>Ganoderma</i> Meroterpenoid Dimers

The first total synthesis of the anti-inflammatory <i>Ganoderma</i> meroterpenoid dimers dispirocochlearoids A-C, along with five of their diastereomers─potential unreported natural products─has been accomplished using a convergent strategy that leveraged common intermediates derived from dayaolingzhiol M. The synthesis features several key steps: a hetero-Diels-Alder reaction, a hydrolysis/double-bond migration cascade to assemble the D/E-bicyclic core, and a condensation/intramolecular aldol/lactonization cascade that constructs the final B/C-bicyclic system of dispirocochlearoids A-C.

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Publication Details

Journal
Organic Letters
Published
2025-12-12
DOI
https://doi.org/10.1021/acs.orglett.5c04234
Primary Topic
Fungal Biology and Applications
Type
article
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article

Biomimetic Total Synthesis of Dispirocochlearoids A–C and Related Ganoderma Meroterpenoid Dimers

Linhai Chen, Xuliang Liu, Fajun Nan, De-Sheng Zhan et al.
Organic Letters
Fungal Biology and Applications
article

Biomimetic Total Synthesis of Dispirocochlearoids A–C and Related Ganoderma Meroterpenoid Dimers

Linhai Chen, Xuliang Liu, Fajun Nan, De-Sheng Zhan, Sheng‐Jie Shi, Lin Yang, Jianpeng Yin
article en

Abstract

The first total synthesis of the anti-inflammatory <i>Ganoderma</i> meroterpenoid dimers dispirocochlearoids A-C, along with five of their diastereomers─potential unreported natural products─has been accomplished using a convergent strategy that leveraged common intermediates derived from dayaolingzhiol M. The synthesis features several key steps: a hetero-Diels-Alder reaction, a hydrolysis/double-bond migration cascade to assemble the D/E-bicyclic core, and a condensation/intramolecular aldol/lactonization cascade that constructs the final B/C-bicyclic system of dispirocochlearoids A-C.

Organic LettersVol. 27(51)
Yantai University (CN), Chinese Academy of Sciences (CN), Shanghai Institute of Materia Medica (CN), National Center for Drug Screening (CN), Advanced Research Institute (US)
Openalex Percentile: Top 57%
Fungal Biology and Applications
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Biomimetic Total Synthesis of Dispirocochlearoids A–C and Related <i>Ganoderma</i> Meroterpenoid Dimers — Linhai Chen, Xuliang Liu, et al. · Organic Letters (2025) | TGRS Research Map | TGRS