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Synthesis of (–)‐Cryptopleurine by Combining Gold(I) Catalysis with a Free Radical Cyclization (Eur. J. Org. Chem. 10/2015)
Author(s) -
Stoye Alexander,
Opatz Till
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201590024
Subject(s) - chemistry , ring (chemistry) , radical cyclization , regioselectivity , heteroatom , palladium , catalysis , medicinal chemistry , stereochemistry , photochemistry , organic chemistry
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).