Improved Enantioselective Synthesis of (-)-Linderol A: Hindered Rotation about Aryl-Csp3 Bond

摘要

An improved enantioselective total synthesis of (-)-linderol A has been achieved via a five-step reaction with a 21% overall yield, starting from phloroacetophenone and (-)-R-phellandrene, two commercially available reagents. In the diastereoselective epoxidation step, the analysis of the two endocyclic epoxide intermediates reveals a hindered sp2-sp3 rotation, which results in rotational diastereoisomers.