Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step

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Title:	Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step
Author:	Scharnagel, Dagmar; Escofet, Imma; Armengol-Relats, Helena; de Orbe, M. Elena; Korber, J. Nepomuk; Echavarren, Antonio M.
Abstract:	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[5.1.0.02,4]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone.
Publication date:	2020-01-08
Subject(s):	54
Rights:	L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/
Pages:	4888 p.
Document type:	Article Article - Accepted version
DOI:	10.1002/anie.201915895
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