Total synthesis of the antiproliferative macrolide (+)-neopeltolide.
A concise total synthesis of the very promising antiproliferative macrolide (+)-neopeltolide (1) has been performed in 16 steps. The main steps of this approach are a Ru(II)-catalyzed alkyne-enal coupling, a Pd0-catalyzed desulfurative cross-coupling, and a stereoselective In(III)-catalyzed propargylation. Four stereogenic centers out of six have been set thanks to substrate-controlled diastereoselective reactions with minimal reliance on protecting groups.
Guinchard
Xavier
X
Centre de Recherche CNRS de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198, Gif-sur-Yvette, France.
Roulland
Emmanuel
E
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008670:Metals / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D018942:Macrolides; D008670:Metals; C519136:neopeltolide