Sarpagine and Related Alkaloids.

Area of Science:

• Natural Product Chemistry
• Organic Synthesis
• Medicinal Chemistry

Background:

• Sarpagine-related alkaloids (macroline and ajmaline) share a common origin and structural features.
• These indole alkaloids are prevalent in the Apocynaceae family, exhibiting diverse biological activities.
• New isolations and asymmetric synthesis are crucial for synthetic and medicinal chemists.

Purpose of the Study:

• To document newly isolated sarpagine-related alkaloids and their properties.
• To present a general and efficient strategy for synthesizing these complex molecules.
• To review synthetic approaches published since 2000.

Main Methods:

• Isolation and characterization of 115 sarpagine-related alkaloids.
• Development of an efficient asymmetric synthesis strategy.
• Application of the asymmetric Pictet-Spengler reaction for tetracyclic template construction.

Main Results:

• Detailed physicochemical properties of 115 newly isolated alkaloids.
• Successful implementation of an efficient strategy for monomeric and bisindole alkaloid synthesis.
• High enantioselectivity (>98% ee) achieved using the asymmetric Pictet-Spengler reaction.

Conclusions:

• The presented strategy offers a scalable route to complex sarpagine-related alkaloids.
• This work expands the knowledge of these natural products and their synthetic accessibility.
• Facilitates further research into the biological properties and potential applications of these alkaloids.