Molecular library synthesis using complex substrates: expanding the framework of triterpenoids

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Synthetic Chemistry

Background:

• Diversity-oriented synthesis (DOS) is crucial for exploring biologically relevant chemical space.
• Traditional DOS often relies on reaction development and catalysis for library diversity.
• Limitations exist in combinatorial-type compound synthesis.

Purpose of the Study:

• To demonstrate a novel DOS strategy utilizing inherent starting material complexity.
• To provide proof of principle for this general approach.
• To conduct a thorough conformational analysis of the generated chemical libraries.

Main Methods:

• Remodeling of a natural product core framework.
• Application of diversity-oriented synthesis (DOS).
• Utilizing inherent complexity of starting materials to control regio- and stereochemistry.

Main Results:

• Proof of principle for a new DOS strategy was established.
• The inherent complexity of starting materials successfully directed regio- and stereochemical outcomes.
• A thorough conformational analysis was performed.

Conclusions:

• A general strategy for chemical library construction using starting material complexity is feasible.
• This approach offers an alternative to traditional DOS methods.
• The strategy enhances access to diverse and biologically relevant chemical space.