Bioactive natural compounds; Enyne metathesis; Skeletal bond reorganization; Ruthenium catalysts; Ring-closing metathesis; Cross-metathesis; Tandem processes; Relay ring-closing; Ring-rearrangement metathesis
Abstract :
[en] 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), ring-rearrangement 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 non-metathesis 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.
Disciplines :
Chemistry
Author, co-author :
Dragutan, Ileana; Acad Romana, Inst Organ Chem, Bucharest 060023, Romania.
Dragutan, Valerian; Acad Romana, Inst Organ Chem, Bucharest 060023, Romania.
Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène
Language :
English
Title :
Enabling Access to Diverse Bioactive Molecules Through Enyne Metathesis Concepts
Publication date :
2013
Journal title :
Current Organic Chemistry
ISSN :
1385-2728
Publisher :
Bentham Science Publishers Ltd., Sharjah, United Arab Emirates
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