The first total syntheses of schilancitrilactones B and C have been accomplished in 17 steps (longest linear sequence) from commercially available materials. Key steps include an intramolecular radical cyclization to provide the seven-membered ring, late-stage iodination, and an intermolecular radical addition reaction to complete the total synthesis.
of main observation and conclusion Schisandraceae triterpenoids are novel natural products that contain highly fused ring systems bearing multiple chiral centers surrounding. Some of them exhibit promising bioactivities, such as antitumor, anti-HIV, etc. In this article, we describe our efforts to the collective total synthesis of schilancidilactones A, B, schilancitrilactones A, B, C, and 20-epi-schilancitrilactone A from common precursors. An intramolecular radical cyclization, late-stage halogenation and AIBN-mediated or Ni-catalyzed intermolecular radical cross coupling reaction were employed as the key steps.www.cjc.wiley-vch.de Scheme 11 Synthetic route to the right frament 9With model substrates 37, 38 and right fragments 9, 39 in hand, Chin.
The cover picture shows Schilancidilactones A, B and Schilancitrilactones A, B, C all belong to schinortriterpenoid. Preliminary bioassay shows some of them possess fascinating bioactivities, such as antitumor, antihepatitis, and anti‐HIV‐1 activities. The total synthesis of Schilancidilactones A, B and Schilancitrilactones A, B, C has been accomplished from the common intermediates for the first time by Tang group. An intramolecular radical cyclization, late‐stage halogenation and AIBN‐mediated or Ni‐catalyzed intermolecular radical cross coupling reaction were employed as the key steps. More details are discussed in the article by Tang et al. on page 255–268.
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