Synthesis 2024; 56(09): 1355-1368
DOI: 10.1055/a-2186-7983
short review

Review of the Total Synthesis of the Aromatic Abietane Diterpenoid Ferruginol

Mengran Li
a   National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. of China
b   State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, P. R. of China
,
Peng Chen
a   National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. of China
,
Haoqi Liu
c   School of Pharmaceutical Sciences, and Guizhou Engineering Laboratory for Synthetic Drugs, Guizhou University, Guiyang, Guizhou 550025, P. R. of China
,
Jian Huang
a   National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. of China
,
Yang Chen
a   National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025, P. R. of China
b   State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100191, P. R. of China
c   School of Pharmaceutical Sciences, and Guizhou Engineering Laboratory for Synthetic Drugs, Guizhou University, Guiyang, Guizhou 550025, P. R. of China
› Institutsangaben
We gratefully acknowledge financial support from the Supported by Guizhou Provincial Science and Technology Projects (Qian Ke He Fundamental ZK[2023-097]), and the State Key Laboratory of Natural and Biomimetic Drugs, Peking University (K202223).


Abstract

The biological properties and synthesis of ferruginol as a classical abietane-type diterpenoid with an aromatic C ring are reviewed. A strategy overview from 1954 to 2023 toward the total synthesis of ferruginol may provide some references for the future design and synthesis of new diterpenoids natural products.

1 Introduction

2 Biological Activity of Ferruginol

3 Strategies toward the Total Synthesis of Ferruginol

3.1 Bogert–Cook Synthesis

3.2 Robinson Annulation

3.3 Domino Synthesis

3.4 Intramolecular Friedel–Crafts Alkylation

3.5 Oxidative Free-Radical Cyclization

3.6 Polyene Cyclization

4 Conclusion and Perspectives



Publikationsverlauf

Eingereicht: 28. Juli 2023

Angenommen nach Revision: 05. Oktober 2023

Accepted Manuscript online:
05. Oktober 2023

Artikel online veröffentlicht:
21. November 2023

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