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Related Experiment Video

Updated: Jul 22, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives

Facile Preparation of 4-Substituted Quinazoline Derivatives

Published on: February 15, 2016

A concise, enantioselective approach to (-)-quinic acid.

Sunil V Pansare¹, Vikrant A Adsool

¹Department of Chemistry, Memorial University of Newfoundland, St. John's, Canada. spansare@mun.ca

Organic Letters

|May 5, 2006

Summary

An efficient enantioselective synthesis provides a key precursor to (-)-quinic acid. This method utilizes a morpholine-dione intermediate and ring-closing metathesis for efficient chiral synthesis.

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

(-)-Quinic acid is a valuable natural product with significant pharmaceutical applications.
Existing synthetic routes to (-)-quinic acid precursors can be lengthy and lack efficiency.

Purpose of the Study:

To develop an expedient and enantioselective synthetic route to a key precursor of (-)-quinic acid.
To establish a novel synthetic strategy employing readily available starting materials.

Main Methods:

Utilized an ephedrine-derived morpholine-dione as a chiral starting material.
Performed a highly diastereoselective conversion of the dione to a dialkenyl morpholinone.
Employed a ring-closing metathesis reaction for cyclization.
Removed the ephedrine auxiliary to yield the enantiomerically enriched product.

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Main Results:

Achieved an expedient, enantioselective synthesis of a crucial (-)-quinic acid precursor.
Demonstrated high diastereoselectivity in the dione-to-dialkenyl morpholinone conversion.
Successfully utilized ring-closing metathesis for efficient synthesis.
Generated an enantiomerically enriched hydroxycyclohexene carboxamide intermediate.

Conclusions:

The developed synthetic strategy is efficient and enantioselective.
This approach provides a viable route to (-)-quinic acid precursors.
The use of ephedrine-derived morpholine-dione offers a practical method for chiral induction.