Synthetic Strategy toward the C44–C65 Fragment of Mirabalin

A convergent and flexible stereoselective synthesis of one isomer of the C44–C65 fragment of mirabalin is described. The key steps include organocatalytic aldolization, ruthenium-catalyzed asymmetric hydrogenation, amide formation, Marshall stereoselective allenylation, and the Nozaki–Hiyama–Kishi r...

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Bibliographic Details
Published in:Organic letters 2014-05, Vol.16 (9), p.2390-2393
Main Authors: Echeverria, Pierre-Georges, Prévost, Sébastien, Cornil, Johan, Férard, Charlène, Reymond, Sébastien, Guérinot, Amandine, Cossy, Janine, Ratovelomanana-Vidal, Virginie, Phansavath, Phannarath
Format: Article
Language:English
Subjects:
Amides - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Chemical Sciences
Hydrogenation
Macrolides - chemical synthesis
Macrolides - chemistry
Macrolides - pharmacology
Molecular Structure
Organic chemistry
Ruthenium - chemistry
Stereoisomerism
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Summary:A convergent and flexible stereoselective synthesis of one isomer of the C44–C65 fragment of mirabalin is described. The key steps include organocatalytic aldolization, ruthenium-catalyzed asymmetric hydrogenation, amide formation, Marshall stereoselective allenylation, and the Nozaki–Hiyama–Kishi reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500720j