Asymmetric epoxidation of gibberellates by the modified Sharpless reagent

Asymmetric epoxidation of methyl gibberellate by the modified Sharpless reagent at various temperature is described.Compound 8 and 9 can be used as the key intermediates for the syntheses of the polyhydroxygibberellins.

Asymmetric Synthesis of Both Enantiomers of Disparlure

Starting from propargyl alcohol （12）, and on the basis of Zhou＇s modified Sharpless asymmetric epoxidation, the sex pheromone of the Gypsy moth, disparlure （＋）-8 and its enantiomer （-）-8 have been synthesized, each in six steps, with overall yields of 29% for （＋）-8 and 27% for （-）-8 （ee〉98%）. The use of the sequential coupling tactic renders the method flexible, which is applicable to the synthesis of other cis-epoxy pheromones.

Concise synthesis of (-)-anisomycin

The antibiotic （-）-anisomycin was synthesized starting from D-tyrosine using Sharpless asymmetric epoxidation as a key reaction followed by formation and hydrolysis of oxazoline set up all chiral center.

Synthetic studies on pseudolaric acid B:Enantioselective synthesis of C4,C10-di-epi-trans-fused[5-7]-bicyclic skeleton

Studies on the synthesis of antifungal and anticancer natural product,pseudolaric acid B,have led to the enantioselective synthesis of di-epi-trans-fused[5-7]-bicyclic co re skeleton.The synthesis was achieved in 10 linear steps,which features the Sharpless asymmetric epoxidation,cyanide-opening reaction of epoxide,and intramolecular[5+2]cycloaddition reaction as the key transformations.The stereochemistry was determined by the X-ray crystallographic analysis.

A total synthesis of (+)-preussin and its 5-epimer

(+)-Preussin (1) and its 5-epimer were synthesized from the divinylcarbinol (3) with Sharpless asymmetric epoxidation of 3 and the oxidative cyclization of 9 with PDC as the key steps.