This invention presents a one-pot method for synthesizing bicyclic acetals from salicylaldehyde, ethyl vinyl ethers, and trimethyl orthoformate, facilitated by Lewis/Bronsted acid. It also introduces an efficient total synthesis approach for myristicyclins A and B, important for their medicinal properties.
Figure (1) formula (I) comprising reacting salicylaldehyde of formula (II) with ethyl vinyl ethers of formula (III) and trimethyl orthoformate in presence of Lewis/Bronsted acid and organic solvent to form an in-situ intermediate of formula (IV) followed by reaction of (IV) with substituted phenols of formula (V). The invention further relates to efficient total synthesis of myristicyclins A and B.
Current methods for synthesizing bicyclic acetals and myristicyclins A and B are complex and inefficient, hindering their widespread production for medicinal purposes.
A streamlined one-pot synthesis enables efficient, protecting-group-free total synthesis of Myristicyclins A and B via a fine-tuned [4+2] cycloaddition and a novel multicomponent cascade cyclization. This regioselective approach offers broad substrate scope, tunable reaction conditions, and gram-scale scalability, ensuring high yield, selectivity, and practical applicability.
The prototype demonstrates a one-pot, gram-scale synthetic method for bicyclic acetals and Myristicyclins A and B using a combination of salicylaldehyde, ethyl vinyl ethers, and trimethyl orthoformate in the presence of Lewis or Brønsted acid catalysts. The reaction proceeds via an in-situ intermediate, which subsequently undergoes cyclization with substituted phenols to yield the desired flavonoid frameworks. This efficient and protecting-group-free process confirms the practicality and reproducibility of the method, offering a scalable route suitable for pharmaceutical and industrial applications.
The basic research stage where fundamental concepts and experimental protocols have been developed. The patent has been and is available for licensing.
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- Facilitates access to biologically active compounds with potential health benefits.
- Offers an efficient route for the synthesis of pharmaceutical intermediates.
- Reduces environmental impact by minimizing chemical waste and energy consumption.
- Enables rapid development of new drug candidates for various diseases.
- Enhances the availability of natural-product-derived medicines.
- Promotes sustainable and cost-effective drug discovery and development.
- Contributes to advancements in organic synthesis methodology.
Organic chemistry, Pharmaceutical industry, Drug synthesis, Chemical research, Medicinal chemistry
Geography of IP
Type of IP
202121026205
460833