Total synthesis of pyranicin.
[Reaction: see text] 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.
Strand
Daniel
D
KTH Chemistry, Organic Chemistry, SE-100 44 Stockholm, Sweden.
Rein
Tobias
T
D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D007783:Lactones; C475590:pyranicin; D010165:Palladium