Complex Polycycles from Simple Propargyl Alcohols through Ruthenium-Catalyzed Cascade Reactions and One-Pot Procedures

Abstract

Multiple bond-forming cascade transformations and one-pot procedures are valuable tools in organic synthesis and drug discovery. These atom-economical processes provide rapid access to natural product-like scaffolds from simple precursors. Herein, we report on ruthenium-catalyzed one-pot conversions of simple 1-alkenyl propargyl alcohols with cyclic 3-ketolactones and dienophiles. Thereby, structurally diverse fused polycycles and functionalized bicyclic structures are accessible from a common precursor with high selectivity. Some of the new drug-like molecules exhibit cytotoxic activity against KB cells.

Key words

atom economy - cascade reactions - dendralenes - homogeneous catalysis - norbornenes - propargyl alcohols - ruthenium

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