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Synthesis of (±)‐ epi ‐Jungianol by the Gold(I)‐Catalyzed Propargyl Claisen Rearrangement/Hydroarylation Cascade Reaction of Propargyl Vinyl Ethers
Author(s) -
Rinaldi Antonia,
Langé Vittoria,
Scarpi Dina,
Occhiato Ernesto G.
Publication year - 2021
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.202001555
Subject(s) - propargyl , chemistry , claisen rearrangement , moiety , vinyl ether , cascade reaction , catalysis , alkyl , organic chemistry , medicinal chemistry , copolymer , polymer
The synthesis of (±)‐ epi ‐jungianol was successfully carried out by the gold(I)‐catalyzed propargyl Claisen rearrangement/hydroarylation cascade reaction of suitably substituted propargyl vinyl ethers as the key step to form the indane skeleton. Two routes were compared, which involved substrates with a different degree of substitution on the vinyl moiety. The one based on a propargyl vinyl ether bearing an unsubstituted vinyl moiety, despite entailing two additional steps, provided the final compound in a higher overall yield. A method for the preparation of acid sensitive propargyl vinyl ethers with an α‐alkyl‐substituted vinyl moiety and their reactivity under gold catalysis is also reported.