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 reaction.
PSL Research University, Chimie ParisTech - CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France.
Pierre-Georges
PG
Echeverria
Sébastien
S
Prévost
Johan
J
Cornil
Charlène
C
Férard
Sébastien
S
Reymond
Amandine
A
Guérinot
Janine
J
Cossy
Virginie
V
Ratovelomanana-Vidal
Phannarath
P
Phansavath
D000577:Amides / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006865:Hydrogenation; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D000970:Antineoplastic Agents; D018942:Macrolides; C000591757:mirabalin; D012428:Ruthenium