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Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step
Author(s) -
Scharnagel Dagmar,
Escofet Imma,
ArmengolRelats Helena,
Orbe M. Elena,
Korber J. Nepomuk,
Echavarren Antonio M.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201915895
Subject(s) - acetylene , cyclopropanation , chemistry , catalysis , ligand (biochemistry) , calcium carbide , medicinal chemistry , acetone , natural product , organic chemistry , combinatorial chemistry , biochemistry , receptor
The gold(I)‐catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)‐1,4‐disubstituted 1,3‐butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user‐friendly procedure. Reaction of acetylene with 1,5‐dienes gives rise stereoselectively to tricyclo[5.1.0.0 2,4 ]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone.