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

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[5.1.0.0^2,4 ]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone.

SUBMITTER: Scharnagel D

PROVIDER: S-EPMC7078946 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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

Scharnagel Dagmar D Escofet Imma I Armengol-Relats Helena H de Orbe M Elena ME Korber J Nepomuk JN Echavarren Antonio M AM

Angewandte Chemie (International ed. in English) 20200131 12

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<sup>2,4</sup> ]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone f ...[more]

PMID: 31912609

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