Synthetic Studies on Isoprenoidquinones. II. Syntheses of Ubiquinone-10, Phylloquinone, and Menaquinone-4 by a Chain-Extending Method Utilizing Terminally Functionalized Isoprenoidhydroquinones

Abstract

Physiologically active polyisoprenoidquinones, ubiquinone-10 (coenzyme Q₁₀), phylloquinone (vitamin K₁), and menaquinone-4 (vitamin K₂₍₂₀₎) were synthesized by a chain-extending method utilizing protected hydroquinones with the omega-hydroxyprenyl or omega-hydroxygeranyl side chain. Conditions for reductive desulfurization subsequent to allylic homologation were investigated.