Consecutive isocyanide-based multicomponent reactions: synthesis of cyclic pentadepsipeptoids

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Synthetic Chemistry

Background:

• Natural products like sansalvamide A serve as inspiration for novel therapeutics.
• Cyclic depsipeptides and depsipeptoids are important scaffolds in drug discovery.
• Efficient synthetic routes are crucial for accessing complex molecular architectures.

Purpose of the Study:

• To develop an efficient and rapid synthetic strategy for cyclic depsipeptoids.
• To synthesize novel cyclic depsipeptoids inspired by the natural product sansalvamide A.
• To establish a versatile methodology for creating diverse cyclic oligodepsipeptoids.

Main Methods:

• Utilized consecutive isocyanide-based multicomponent reactions.
• Employed Ugi and Passerini reactions in a streamlined sequence.
• Developed a synthetic strategy for six-membered cyclic depsipeptoids.

Main Results:

• Successfully synthesized six cyclic depsipeptoids.
• Demonstrated an efficient and fast synthetic approach.
• Established the versatility of the developed methodology.

Conclusions:

• The developed methodology offers a powerful tool for the synthesis of cyclic depsipeptoids.
• This approach enables access to a wide range of cyclic oligodepsipeptoid structures.
• The synthetic strategy is inspired by the natural depsipeptide sansalvamide A.