Synthesis of the EFG-ring system of pectenotoxin-4

Thesis

The EFG-ring system of pectenotoxin-4 was synthesised via a novel pathway which ultilised a cobalt-mediated oxidative cyclisation to access the trans F-ring, and an osmium-mediated oxidative cyclisation to form the cis E-ring.

Subsequent union of these fragments, under modified Julia-Kocienski olefination conditions, facilitated the synthesis of the EFG-ring system of pectenotoxin-4.

Introduction

This chapter reports the previous total syntheses of pectenotoxin molecules, along with completed syntheses of pectenotoxin fragments, including the Donohoe group’s synthesis of the ABC-ring system of pectenotoxin-4.

Results and Discussion

The synthesis of the FG-ring system and subsequent coupling to the E-ring fragment are detailed in this chapter. The final steps from the Julia adduct to the EFG-ring system conclude this chapter.

Authors: Roushanbakhti, A

• Type of award: DPhil
• Level of award: Doctoral
• Awarding institution: University of Oxford