Synthetic strategy toward the C44-C65 fragment of mirabalin

Pierre-Georges Echeverria; Sébastien Prévost; Johan Cornil; Charlène Férard; Sébastien Reymond; Amandine Guérinot; Janine Cossy; Virginie Ratovelomanana-Vidal; Phannarath Phansavath

doi:10.1021/ol500720j

Synthetic strategy toward the C44-C65 fragment of mirabalin

Org Lett. 2014 May 2;16(9):2390-3. doi: 10.1021/ol500720j. Epub 2014 Apr 11.

Authors

Pierre-Georges Echeverria¹, Sébastien Prévost, Johan Cornil, Charlène Férard, Sébastien Reymond, Amandine Guérinot, Janine Cossy, Virginie Ratovelomanana-Vidal, Phannarath Phansavath

Affiliation

¹ PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France.

PMID: 24725196
DOI: 10.1021/ol500720j

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology
Hydrogenation
Macrolides / chemical synthesis*
Macrolides / chemistry
Macrolides / pharmacology
Molecular Structure
Ruthenium / chemistry
Stereoisomerism

Substances

Amides
Antineoplastic Agents
Macrolides
mirabalin
Ruthenium