Synthesis of Enantiomerically Pure (8S,9S,10R,6Z)-Trihydroxyoctadec-6-enoic Acid

Abstract

We have accomplished the asymmetric synthesis of (8S,9S,10R,6Z)-trihydroxyoctadec-6-enoic acid in optically pure form and determined the absolute configuration of the natural product on the basis of the stereodetermined chiral building block 7, which was prepared by the catalytic enantioselective allylic oxidation of 4,5-epoxycyclohex-1-ene using an S-configured N,N-bidentate ligand-copper catalyst.

Regiodivergent Desymmetrization Reaction of meso-Azabicycloheptene Providing Two Enantioenriched Structural Isomers

“…These chiral building blocks are useful intermediates for synthesizing (−)-oseltamivir phosphate (Tamiflu) and its derivatives. Furthermore, after ozonolysis, a variety of acyclic natural and unnatural products can be synthesized using these chiral building blocks…”