2020ChemCatChemOpen access

Transformations of bio‐sourced 4‐hydroxyphenylpropanoids based on olefin metathesis

Hallouma Bilel, Naceur Hamdi, Cédric Fischmeister, Christian Bruneau

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Abstract

Abstract 4‐Hydroxyphenylpropanoids represent an important class of natural products directly extracted from plants or derived from lignocelullosic materials. They are phenol derivatives equipped with a terminal propenyl group, which is perfectly suited for applications involving olefin metathesis processes. In this review, we show that conditions have been found to achieve their self‐metathesis, cross metathesis as well as some sequential transformations with metathesis as a key step with high yields and controlled stereoselectivities. Some applications in multi‐step synthesis of biological relevant natural products involving metathetic transformations of 4‐hydroxyphenylpropanoids are also reported.

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Abstract 4‐Hydroxyphenylpropanoids represent an important class of natural products directly extracted from plants or derived from lignocelullosic materials. They are phenol derivatives equipped with a terminal propenyl group, which is perfectly suited for applications involving olefin metathesis processes. In this review, we show that conditions have been found to achieve their self‐metathesis, cross metathesis as well as some sequential transformations with metathesis as a key step with high yields and controlled stereoselectivities. Some applications in multi‐step synthesis of biological relevant natural products involving metathetic transformations of 4‐hydroxyphenylpropanoids are also reported.

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Available abstract

Abstract 4‐Hydroxyphenylpropanoids represent an important class of natural products directly extracted from plants or derived from lignocelullosic materials. They are phenol derivatives equipped with a terminal propenyl group, which is perfectly suited for applications involving olefin metathesis processes. In this review, we show that conditions have been found to achieve their self‐metathesis, cross metathesis as well as some sequential transformations with metathesis as a key step with high yields and controlled stereoselectivities. Some applications in multi‐step synthesis of biological relevant natural products involving metathetic transformations of 4‐hydroxyphenylpropanoids are also reported.

Key concepts: Metathesis, Olefin metathesis, Acyclic diene metathesis, Salt metathesis reaction, Ring-opening metathesis polymerisation, Phenol, Chemistry, Organic chemistry

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