Article (Scientific journals)
Olefin metathesis as key step in the synthesis of bioactive compounds: Challenges in the total synthesis of irioteolides
Demonceau, Albert; Dragutan, I.; Dragutan, V. et al.
2012In Current Organic Synthesis, 9, p. 779-790
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Keywords :
Homogeneous catalysis; Iriomoteolides; Macrocyclisation; Olefin metathesis; Macrolide; Ruthenium catalysts
Abstract :
[en] Iriomoteolides are novel macrolides possessing either a unique 15-membered or a 20-membered macrocycle, and displaying exceedingly potent cytotoxicity with IC50 values of up to 2 ng/mL. Thus far, over a period of about four years, ten research groups worldwide have published their synthetic efforts resulting in four total syntheses of iriomoteolides and a few diastereomers thereof, and a number of fragment and macrocyclic core syntheses. Interestingly, three total syntheses involved ring-closing metathesis as the key step for the construction of the macrocycle, whereas the synthesis of three fragments was accomplished using a cross-metathesis reaction. Herein we highlight assets and limitations of the olefin metathesis reaction in the synthesis of the title compounds.
Disciplines :
Chemistry
Author, co-author :
Demonceau, Albert ;  Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Dragutan, I.;  Institute of Organic Chemistry of the Romanian Academy, 202B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania
Dragutan, V.;  Institute of Organic Chemistry of the Romanian Academy, 202B Spl. Independentei, P.O. Box 35-108, 060023 Bucharest, Romania
Le Gendre, Pierre
Language :
English
Title :
Olefin metathesis as key step in the synthesis of bioactive compounds: Challenges in the total synthesis of irioteolides
Publication date :
2012
Journal title :
Current Organic Synthesis
ISSN :
1570-1794
Publisher :
Bentham Science Publishers, United Arab Emirates
Volume :
9
Pages :
779-790
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 29 August 2012

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