New Route to Complex Polycyclic Molecules

New Route to Complex Polycyclic Molecules

Author: Angewandte Chemie International Edition

Structurally complex molecules can be expensive and time-consuming to prepare. They require starting materials that are both readily accessible and sufficiently reactive to undergo multiple bond-forming events.

Andrew Lawrence, Fernanda Duarte, and colleagues, University of Edinburgh, UK, have developed a domino reaction sequence by which readily available para-quinols are transformed into highly complex polycyclic molecules. Para-quinols are stable under ambient conditions. However, when treated with an amine catalyst and heated in chloroform, they dimerize efficiently and undergo a series of bond-forming reactions to form tetracycles. A final oxa-Michael addition occurs in the presence of a strong base. It forms a hexacycle containing four new bonds, four new rings, and eight new contiguous stereogenic centers (see scheme).

Reaction Scheme

The tetracycles are accessible in gram-scale quantities, which allows further functionalization of the complex structures. The team suggests that the method could be used to prepare libraries of natural-product-like compounds.


 

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