European Journal of Organic Chemistry
Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Synthesis of (–)-Cryptopleurine by Combining Gold(I) Catalysis with a Free Radical Cyclization (Eur. J. Org. Chem. 10/2015)
The cover picture shows how the core of (–)-cryptopleurine was assembled by using a palladium-catalyzed cross coupling (cyan bond), a gold-catalyzed cyclization (yellow bond) and a radical cyclization (green bond). While the alkaloid itself was very light-sensitive and the fires of Mordor were not required for its degradation, the ring-shaped gold–NHC complex employed in the key cyclization step was crucial to achieve high regioselectivity. Literally, it was the “One Ring to rule them all”. Details are discussed in the article by A. Stoye and T. Opatz on 2149 ff. The background image (taken by Manfred Werner) shows the atmospheric glow of oxygen and nitrogen, the two kinds of heteroatoms present in cryptopleurine, in a polar light. The font for the Elvish runes on The One Ring was provided by Johan Winge, publication was kindly permitted by C. Blackburn (Tolkien Estate).