Synthesis of pyragonicin.
[structure: see text] A stereocontrolled convergent synthesis of the annonaceous acetogenin pyragonicin (1) is presented. The key intermediates were accessed using asymmetric Horner-Wadsworth-Emmons (HWE) methodology. A reagent controlled zinc-mediated stereoselective coupling, joining the two highly functionalized intermediates 3 and 4, then provided the core structure.
Strand
Daniel
D
KTH Chemistry, Organic Chemistry, SE-100 44 Stockholm, Sweden.
Rein
Tobias
T
D054378:Acetogenins; D029061:Annonaceae / Q000737:chemistry; D005233:Fatty Alcohols / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D054378:Acetogenins; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; C509193:pyragonicin; D015032:Zinc