Collective Synthesis of Schilancidilactones A, B and Schilancitrilactones A, B, C, 20‐epi‐Schilancitrilactone A1. Issue 3 (6th February 2019)

• Record Type: Journal Article
• Authors: Wang, Hengtao; Wang, Liang; Li, Yihang; Zhang, Xiunan; Tang, Pingping
• Is Part Of: Chinese journal of chemistry. Volume 37:Issue 3(2019)
• Page Start: 255
• Page End: 268
• Publication Date: 2019-02-06
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201800557
• Languages: English
• ISSNs: 1001-604X

Abstract

Summary 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. Abstract : The collective total synthesis of schilancidilactones A, B, schilancitrilactones A, B, C, and 20‐ epi ‐schilancitrilactone A were accomplished. The key steps include intermolecular radical cyclization, late‐stage halogenation, intermolecular cross coupling of alkyl halide with vinyl stannane.