Quinic acid as a chiron in total synthesis

Area of Science:

• Organic Chemistry
• Asymmetric Synthesis
• Medicinal Chemistry

Background:

• Quinic acid is a naturally occurring compound with a rich stereochemical structure.
• It has emerged as a valuable and accessible chiral building block in synthetic chemistry.
• Its functionalized scaffold is crucial for constructing complex molecular architectures.

Purpose of the Study:

• To provide a comprehensive review of synthetic strategies employing quinic acid.
• To cover the period from the 1980s up to 2025.
• To underscore the enduring significance of quinic acid in modern organic synthesis.

Main Methods:

• Literature review of synthetic methodologies.
• Analysis of quinic acid's application in synthesizing diverse compound classes.
• Identification of trends in quinic acid-based synthesis.

Main Results:

• Quinic acid serves as a versatile scaffold for synthesizing carbocyclic frameworks, vitamin D analogues, carbasugars, cyclitols, aminocyclitols, lactones, alkaloids, and macrocyclic fragments.
• Synthetic strategies have evolved significantly over the past four decades.
• Its utility spans the creation of numerous natural products and bioactive compounds.

Conclusions:

• Quinic acid remains a pivotal chiral building block for complex molecule synthesis.
• Ongoing research continues to expand its applications in asymmetric synthesis.
• Its accessibility and stereochemical richness ensure its continued importance in organic chemistry.