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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Formal synthesis of (-)-neopeltolide featuring a highly stereoselective oxocarbenium formation/reduction sequence
Dionicio Martinez-Solorio1, Michael P Jennings
1Department of Chemistry, 250 Hackberry Lane, The University of Alabama, Tuscaloosa, Alabama 35487-0336, USA.
Abstract:
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.
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