Aziridine-based concise synthesis of (±)-alstonerine

Area of Science:

• Organic Chemistry
• Natural Product Synthesis
• Medicinal Chemistry

Background:

• Macroline-related alkaloids, such as (±)-alstonerine, are complex natural products with potential biological activities.
• Efficient synthetic routes are crucial for accessing these compounds for further study and development.

Purpose of the Study:

• To develop a concise and efficient synthetic strategy for the macroline-related alkaloid (±)-alstonerine.
• To explore key chemical transformations for constructing the alkaloid core structure.

Main Methods:

• Regioselective and stereospecific aziridine ring-opening using a sulfone-stabilized carbanion.
• Me3Al-mediated O → N-transacylation-elimination reaction.
• Intramolecular Michael reaction for carbon-carbon bond formation.
• One-pot reduction-dehydration-Pictet-Spengler cyclisation for indole ring formation.

Main Results:

• Successful concise synthesis of (±)-alstonerine achieved.
• Key steps demonstrated high regioselectivity and stereospecificity.
• The developed route offers an efficient pathway to the target alkaloid.

Conclusions:

• The reported synthesis provides a valuable method for accessing (±)-alstonerine.
• The key transformations employed are applicable to the synthesis of related alkaloids.
• This work contributes to the field of natural product synthesis and medicinal chemistry.