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Schinortriterpenoids: A Case Study in Synthetic Design.

Xin Li1, Paul Ha-Yeon Cheong1, Rich G Carter1

  • 1Chemistry Department, Oregon State University, Gilbert Hall Room 153, Corvallis, OR, 9733I, USA.

Angewandte Chemie (International Ed. in English)
|January 19, 2017
PubMed
Summary

This review details the total synthesis of complex schinortriterpenoids, evaluating strategies for constructing polycyclic natural product scaffolds. It analyzes six syntheses, offering insights into advanced organic chemistry approaches.

Keywords:
asymmetric synthesisnatural productsschinortriterpenoidstotal synthesis

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Medicinal Chemistry

Background:

  • Guiding principles for total synthesis planning have evolved since the advent of retrosynthetic analysis.
  • Complex natural products serve as crucial benchmarks for evaluating and advancing synthetic methodologies.
  • The schinortriterpenoid family represents a recent class of complex polycyclic natural products attracting significant synthetic interest.

Purpose of the Study:

  • To provide a comprehensive overview of the synthetic efforts towards the schinortriterpenoid family.
  • To analyze and compare the diverse synthetic strategies employed in the construction of these complex scaffolds.
  • To evaluate the application of established synthetic principles in the context of novel natural product architectures.

Main Methods:

  • Literature review and analysis of reported total syntheses of schinortriterpenoids.
  • Comparative assessment of synthetic routes, focusing on key transformations and strategic disconnections.
  • Discussion of challenges and innovations in constructing the polycyclic core structures.

Main Results:

  • Six total syntheses of schinortriterpenoids have been reported in the literature.
  • Varied synthetic strategies, including different retrosynthetic analyses and key bond-forming reactions, have been utilized.
  • The syntheses highlight advancements in stereoselective synthesis and the construction of intricate polycyclic systems.

Conclusions:

  • The synthetic endeavors towards schinortriterpenoids demonstrate the power of established synthetic principles in tackling complex molecular targets.
  • Comparative analysis reveals key strategic decisions that facilitate the efficient construction of these natural products.
  • This body of work provides valuable lessons for future synthetic campaigns targeting complex polycyclic natural products.