Beilstein J. Org. Chem.2022,18, 1625–1628, doi:10.3762/bjoc.18.173
Provincial Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen, Guangdong 518055, China 10.3762/bjoc.18.173 Abstract An approach to aberrarone, an antimalarial diterpenoid natural product with tetracyclic skeleton is reported. Key to the stereoselective preparation of
the 6-5-5 tricyclic skeleton includes the mediation of Nagata reagent for constructing the C1 all-carbon quaternary centers and gold-catalyzed cyclopentenone synthesis through C–H insertion.
Keywords: aberrarone; C–H insertion; gold; Pauson–Khand; total synthesis; Introduction
Marine natural
antitumor, antituberculosis and antimalarial activities [2][3][4][5][6]. Among these structurally intriguing natural products, aberrarone (1) shows antimalarial activity against the chloroquine-resistant strain of Plasmodium falciparum (IC50 = 10 μg/mL) [7]. Structurally, aberrarone possesses an unusual
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Graphical Abstract
Figure 1:
Selected representative natural products with 6-5-5 tricyclic skeleton.