Studies of the biomimetic synthesis of plumarellide

Student thesis: MRes Thesis

Abstract

Part 1 provides an overview of marine natural products, emphasizing the
significance of polycyclic cerium diterpenes, specifically furanobutenolidebased cembranoids (FBCs), due to their unique structures and diverse
biological activities. These compounds, often found in corals, are of great
research interest, but their limited natural sources hinder extensive study. Thus,
the total synthesis of FBCs is crucial. Researchers have explored various
methods, including biomimetic synthesis, computational chemistry, and
organic synthetic chemistry, to address this challenge.
Part 2 introduces one FBCs molecule, plumarellide, which remains
unsynthesized. Plumarellide is distinct with a central cyclohexene ring linked
to a substituted cyclohexane and an oxybridged cyclohexene. It is related to
three other natural product molecules also isolated from corals. Multiple
research groups have attempted to synthesize plumarellide, simulating its
biosynthetic pathway and proposing thermodynamically favorable synthetic
routes using computational chemistry. However, full synthesis has not yet
been achieved.
Part 3 presents a new approach to the total synthesis of plumarellide. This
method involves the organic synthesis of a key precursor, 24, followed by
biomimetic synthesis and computational chemistry-assisted transformations
leading to the final product. The article provides detailed explanations of the
implemented synthesis steps and their significance in the context of
plumarellide synthesis.
Part 4 outlines the future research endeavors. While a potential full synthesis
route has been designed, it requires further experimentation and refinement. If
the attempt to fully synthesize plumarellide proves successful, this achievement
will serve as a valuable foundation for synthesizing three other related natural
products found within the same organism. Additionally, research into structural
modifications of these natural products and subsequent biological activity testing
holds promising prospects. The article looks ahead to these exciting possibilities
in the field of natural product synthesis and modification.
Date of AwardMar 2024
Original languageEnglish
Awarding Institution
  • University of Nottingham
SupervisorHainam Do (Supervisor), Bencan Tang (Supervisor) & Kam Loon Fow (Supervisor)

Keywords

  • biomimetic synthesis
  • Plumarellide

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