Total synthesis of (?)-panduratin D?

Chemical Communications Pub Date: 2022-07-05 DOI: 10.1039/D2CC02980D

Abstract

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.

Graphical abstract: Total synthesis of (?)-panduratin D
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