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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
An efficient formal synthesis of (-)-clavosolide a featuring a "mismatched" stereoselective oxocarbenium reduction
Jesse D Carrick1, Michael P Jennings
1Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487-0336, USA.
Abstract:
The enantioselective formal synthesis of the polyketide marine natural product (-)-clavosolide A is presented. The construction of the beta-C-glycoside subunit is highlighted by a one-pot oxocarbenium cation formation/reduction sequence. Yamaguchi dimerization afforded the diolide aglycon in 18 steps (longest linear sequence).
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