Total Synthesis of Schilancitrilactones B and C

  • Author: Veronika Belusa
  • Published Date: 19 March 2015
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Total Synthesis of Schilancitrilactones B and C

Schilancitrilactones B and C were isolated in 2012 by Sun and co-workers from the stems of Schisandra Lancifolia [1], which have been used in traditional Chinese medicine for the treatment of neurasthenia and related diseases. Preliminary biological assays indicated that schilancitrilactone C showed biological activities for inhibiting HIV-1 while schilancitrilactone B was not bioactive.

Pingping Tang and colleagues, Nankai University, Tianjin, China, have accomplished the first total syntheses of schilancitrilactones B and C. They started from commercially available materials and needed 17 steps (longest linear sequence). The key steps include the successful implementation of an intramolecular radical cyclization to prepare a seven-member ring, late-stage iodination, and an intermolecular radical C–C bond formation.

The researchers say that their approach provides a sequence for the syntheses of compounds related to the schilancitrilactones, as well as their derivatives and analogues.



[1] Schilancitrilactones A–C: Three Unique Nortriterpenoids from Schisandra lancifolia,
Xiao Luo, Yi-Ming Shi, Rong-Hua Luo, Shi-Hong Luo, Xiao-Nian Li, Rui-Rui Wang, Sheng-Hong Li, Yong-Tang Zheng, Xue Du, Wei-Lie Xiao, Jian-Xin Pu, Han-Dong Sun,
Org. Lett. 2012, 14, 1286–1289.
DOI: 10.1021/ol300099e

 

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