1229648-41-2Relevant articles and documents
Formal synthesis of (-)-Neopeltolide featuring a highly stereoselective oxocarbenium formation/reduction sequence
Martinez-Solorio, Dionicio,Jennings, Michael P.
experimental part, p. 4095 - 4104 (2010/09/11)
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 δ-lactone. Central to the synthetic approach is a tandem nucleophilic addition-diastereoselective axial reduction of an in situ generated oxocarbenium cation to assemble the β-C-glycoside moiety of the neopeltolide core.