Issue 61, 2022

Total synthesis of (−)-panduratin D

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

Supplementary files

Article information

Article type
Communication
Submitted
26 May 2022
Accepted
04 Jul 2022
First published
05 Jul 2022

Chem. Commun., 2022,58, 8564-8567

Total synthesis of (−)-panduratin D

S. R. Bavikar, H. Lo, C. N. S. Sai Pavan Kumar and R. Chein, Chem. Commun., 2022, 58, 8564 DOI: 10.1039/D2CC02980D

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