Access to a Structurally Complex Compound Collection via Ring Distortion of the Alkaloid Sinomenine

Many compound collections used in
high-throughput screening are
composed of members whose structural complexity is considerably lower
than that of natural products. We previously reported a strategy for
the synthesis of complex and diverse small molecules from natural
products using ring-distortion reactions, called complexity-to-diversity
(CtD), and herein, CtD is applied in the synthesis of 16 diverse scaffolds
and 65 total compounds from the alkaloid natural product sinomenine.
Chemoinformatic analysis shows that these compounds possess complex
ring systems and marked three-dimensionality.