Total Synthesis of (–)-Panduratin D

Herein, an enantioselective total synthesis of (–)-panduratin D, a
novel secondary metabolite against human pancreatic PANC-1
cancer cell, from commercially available 3-methoxyphenol is
reported. The synthesis was completed in nine steps and the key
features include Sonogashira coupling, anionic Snieckus−Fries
rearrangement, directed ortho metalation, tandem Si → C Alkyl
rearrangement/Claisen−Schmidt condensation, and chiral boron
complex-promoted asymmetric Diels–Alder cycloaddition. These
endeavors could facilitate the biological studies of (–)-panduratin D
and its analogs