Intramolecular cycloaddition leads to the pentacyclic core of cortistatins

Synthesising intriguing bioactive natural products in the most expedient and atom-efficient manner remains a highly active and competitive field of research. Cortistatins A and J, first isolated from the marine sponge Corticium simplex in 2006, have been identified as effective anti-angiogenics, which studies have found could suppress cancer recurrence when given in conjunction with traditional cancer drugs.

Lok Lok Liu and Pauline Chiu at the University of Hong Kong have reported a concise, high yielding, asymmetric synthesis of the pentacyclic framework of the cortistatins, in 12 steps from commercially available starting materials. Their synthesis employs a highly diastereoselective intramolecular [4+3] cycloaddition of epoxy enolsilanes as the key step and brings them close to their ultimate goal.

To find out more, download the ChemComm communication for free up until March 28th

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