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Total Synthesis of the Marine Natural Product Parazoanthine F by Copper‐Mediated C–N Coupling
Author(s) -
Wefer Johannes,
Lindel Thomas
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.201500823
Subject(s) - chemistry , natural product , moiety , amide , cerium , yield (engineering) , alkene , total synthesis , ammonium nitrate , bromide , medicinal chemistry , allene , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
The total synthesis of the marine natural product parazoanthine F from the sea anemone Parazoanthus axinellae is described. The key problem was the assembly of an N ‐styrylhydantoin moiety. It was possible to cleanly hydroxylate the benzylic position of the corresponding phenethyl unit by treatment with cerium ammonium nitrate. However, elimination to the alkene proved to be surprisingly difficult. The breakthrough came after optimizing the CuI/ N , N′ ‐dimethylethylenediamine‐mediated C–N coupling of a 2,2,4,6,7‐pentamethyl‐5‐sulfonyl‐dihydrobenzofuran‐protected arginine amide with p ‐methoxystyryl bromide under microwave conditions (70 °C, 200 W) in the presence of Cs 2 CO 3 . Our studies culminated in a short approach with an overall yield of about 12 %.