Formal synthesis of (-)-neopeltolide featuring a highly stereoselective oxocarbenium formation/reduction sequence.
The formal synthesis of the unnatural (-)-neopeltolide core is discussed in detail. Efficient application of the Evans' protocol for the synthesis of 1,3-syn-diols via an intramolecular hetero-Michael addition followed by reductive deprotection of the resulting benzylidene acetal allowed for swift access to the delta-lactone. Central to the synthetic approach is a tandem nucleophilic addition-diastereoselective axial reduction of an in situ generated oxocarbenium cation to assemble the beta-C-glycoside moiety of the neopeltolide core.
Martinez-Solorio
Dionicio
D
Department of Chemistry, 250 Hackberry Lane, The University of Alabama, Tuscaloosa, Alabama 35487-0336, USA.
Jennings
Michael P
MP
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D018942:Macrolides; C519136:neopeltolide