De novo asymmetric syntheses of muricatacin and its analogues via dihydroxylation of dienoates.
A short and highly efficient route to both enantiomers of muricatacin as well as the C-5-epimer has been developed. The key to the overall transformation is the highly regio- and enantioselective Sharpless asymmetric dihydroxylation of an (E,Z)-dienoate. The highly efficient stereoselective synthesis prepares (-)-muricatacin in seven steps and 66% overall yield.
Ahmed
Md Moinuddin
MM
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Cui
Hu
H
O'Doherty
George A
GA
D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D005663:Furans; C510913:L-talo-gamma-lactone; D007783:Lactones; C082488:muricatacin