Total Synthesis of Pyranicin
journal contributionposted on 20.01.2005, 00:00 by Daniel Strand, Tobias Rein
A stereocontrolled convergent synthesis of the annonaceous acetogenin pyranicin (1) is presented. Asymmetric Horner−Wadsworth−Emmons (HWE) reactions were used to access key intermediates. The tetrahydropyran derivative 2 was obtained via an asymmetric desymmetrization of the meso-dialdehyde 6, and the butenolide fragment was constructed using a stereoconvergent reaction sequence involving a parallel kinetic HWE resolution followed by a Pd-catalyzed allylic substitution. The C10/C15 1,6-diol motif was installed using Carreira's asymmetric acetylide addition methodology.
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diolmotifacetylide addition methodologyPyranicindesymmetrizationAsymmetricallylicCarreiraaccessintermediatestereocontrolled convergent synthesisdialdehyde 6HWE resolutionbutenolide fragmentstereoconvergent reaction sequencetetrahydropyranannonaceous acetogenin pyranicinmesosubstitutionHornerTotal Synthesis