Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

Terpene compounds probably represent the most diversified class of secondary metabolites. Some classes of terpenes, mainly diterpenes (C20) and sesterterpenes (C25) and to a lesser extent sesquiterpenes (C15), share a common bicyclo[3.6.0]undecane core which is characterized by the presence of a cyc...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2023, Vol.19 (1), p.245-281
Main Authors: Alleman, Cécile, Gadais, Charlène, Legentil, Laurent, Porée, François-Hugues
Format: Article
Language:English
Subjects:
5-8 bicycle
Catalysis
Chemical Sciences
Chemistry
cyclization strategies
Cyclopentane
Diterpenes
Fungi
Metabolites
Natural products
Review
Secondary metabolites
Sesquiterpenes
Terpenes
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Summary:Terpene compounds probably represent the most diversified class of secondary metabolites. Some classes of terpenes, mainly diterpenes (C20) and sesterterpenes (C25) and to a lesser extent sesquiterpenes (C15), share a common bicyclo[3.6.0]undecane core which is characterized by the presence of a cyclooctane ring fused to a cyclopentane ring, i.e., a [5-8] bicyclic ring system. This review focuses on the different strategies elaborated to construct this [5-8] bicyclic ring system and their application in the total synthesis of terpenes over the last two decades. The overall approaches involve the construction of the 8-membered ring from an appropriate cyclopentane precursor. The proposed strategies include metathesis, Nozaki-Hiyama-Kishi (NHK) cyclization, Pd-mediated cyclization, radical cyclization, Pauson-Khand reaction, Lewis acid-promoted cyclization, rearrangement, cycloaddition and biocatalysis.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.19.23