Abstract
This paper surveys recent advances in valorization of transition-metal-catalyzed enyne metathesis as key events in the total synthesis of naturally occurring compounds of biological and medicinal importance. Special attention is devoted to methodologies based on dienyne ring-closing metathesis (RCM) applied in tandem and sequential processes, on relay ring-closing metathesis (RRCM), ringrearrangement metathesis (RRM), enyne cross-metathesis (CM) and enyne skeletal bond reorganization, all proceeding under metalcarbenes (Ru or Mo alkylidenes) or metal-salts (Pd or Pt) catalysis. The high potential of these procedures in constructing versatile scaffolds as essential structural cores of a diversity of bioactive natural products is highlighted. Inventive functionalizations by nonmetathesis transformations intervening in the total synthesis of the targeted natural compounds, prior to (Michael addition, Wittig olefination, allylation etc.) or after (Diels-Alder cycloaddion, Heck and Suzuki-Miyaura reactions, Dess-Martin oxidation, dihydroxylation, epoxidation etc.) the pivotal metathesis step have also been included.
Keywords: Bioactive natural compounds, Enyne metathesis, Skeletal bond reorganization, Ruthenium catalysts, Ring-closing metathesis, Cross-metathesis, Tandem processes, Relay ring-closing, Ring-rearrangement metathesis.
Current Organic Chemistry
Title:Enabling Access to Diverse Bioactive Molecules Through Enyne Metathesis Concepts
Volume: 17 Issue: 22
Author(s): Ileana Dragutan, Valerian Dragutan, Albert Demonceau and Lionel Delaude
Affiliation:
Keywords: Bioactive natural compounds, Enyne metathesis, Skeletal bond reorganization, Ruthenium catalysts, Ring-closing metathesis, Cross-metathesis, Tandem processes, Relay ring-closing, Ring-rearrangement metathesis.
Abstract: This paper surveys recent advances in valorization of transition-metal-catalyzed enyne metathesis as key events in the total synthesis of naturally occurring compounds of biological and medicinal importance. Special attention is devoted to methodologies based on dienyne ring-closing metathesis (RCM) applied in tandem and sequential processes, on relay ring-closing metathesis (RRCM), ringrearrangement metathesis (RRM), enyne cross-metathesis (CM) and enyne skeletal bond reorganization, all proceeding under metalcarbenes (Ru or Mo alkylidenes) or metal-salts (Pd or Pt) catalysis. The high potential of these procedures in constructing versatile scaffolds as essential structural cores of a diversity of bioactive natural products is highlighted. Inventive functionalizations by nonmetathesis transformations intervening in the total synthesis of the targeted natural compounds, prior to (Michael addition, Wittig olefination, allylation etc.) or after (Diels-Alder cycloaddion, Heck and Suzuki-Miyaura reactions, Dess-Martin oxidation, dihydroxylation, epoxidation etc.) the pivotal metathesis step have also been included.
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Cite this article as:
Dragutan Ileana, Dragutan Valerian, Demonceau Albert and Delaude Lionel, Enabling Access to Diverse Bioactive Molecules Through Enyne Metathesis Concepts, Current Organic Chemistry 2013; 17 (22) . https://dx.doi.org/10.2174/13852728113179990113
DOI https://dx.doi.org/10.2174/13852728113179990113 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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