Efficient Synthesis of (<i>E</i>)-Vinylgermanes via Stille Cross-Coupling Reaction from 1-Tributylstannyl-2-trialkyl(triphenyl)germylethylenes

David-Quillot, Franck; Marsacq, Didier; Balland, Alexia; Thibonnet, J.; Abarbri, Mohamed; Duchêne, Alain

doi:10.1055/s-2003-37358

Synthesis

2003

DOI: 10.1055/s-2003-37358

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Efficient Synthesis of (E)-Vinylgermanes via Stille Cross-Coupling Reaction from 1-Tributylstannyl-2-trialkyl(triphenyl)germylethylenes

Franck David-Quillot¹,

Didier Marsacq²,

Alexia Balland³

et al.

Abstract: The transfer of a β-vinylgermyl synthon is easily achieved by Stille reaction using (E)-1-tributylstannyl-2-trialkyl(or triphenyl)germylethylenes. With this methodology good yields of (E)-aryl or heteroarylvinylgermanes, stereodefined germyldienoic acids, and germyl α,β-enones are obtained from acid chlorides.

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Total Synthesis of the Reported Structure of Neaumycin B

Ding

Smith

2023

J. Am. Chem. Soc.

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The stereoselective total synthesis of structure 1 assigned to the macrolide natural product neaumycin B is reported in a 2.3% overall yield on 90 mg scale. The synthesis features a gram-scale nickel-catalyzed reductive cross-coupling/spiroketalization tactic to construct the spiroketal core of neaumycin B. The stereostructures of the C3–C6, C8–C14, and C20–C41 segments of synthetic neaumycin B were unambiguously verified by X-ray crystallography.

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Total Synthesis of the Reported Structure of Neaumycin B

Ding

Smith

2023

J. Am. Chem. Soc.

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Radical Germylzincation of α-Heteroatom-Substituted Alkynes

et al. 2018

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The regio-and stereoselective addition of germanium and zinc across the CC triple bond of nitrogen-, sulfur-, oxygen-, and phosphorous-substituted terminal and internal alkynes is achieved by reaction with a combination of R 3 GeH and Et 2 Zn. Diagnostic experiments support a radical-chain mechanism and the -zincated vinylgermanes that show exceptional stability are characterized by NMR spectroscopy and X-ray crystallography. The unique feature of this new radical germylzincation reaction is that the C(sp 2)-Zn bond formed remains available for subsequent in situ Cu(I)-or Pd(0)-mediated CC or C-heteroatom bond formation with retention of the double bond geometry. These protocols offer a modular access to elaborated tri-and tetrasubstituted vinylgermanes decorated with heteroatom substituents  to germanium that are useful for the preparation of stereodefined alkenes. Additional data and discussion, experimental details, NMR spectra for new compounds, and X-ray crystal structures (PDF) Crystallographic information files (CIF)

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Efficient Synthesis of (E)-Vinylgermanes via Stille Cross-Coupling Reaction from 1-Tributylstannyl-2-trialkyl(triphenyl)germylethylenes

Cited by 2 publications

References 1 publication

Total Synthesis of the Reported Structure of Neaumycin B

Total Synthesis of the Reported Structure of Neaumycin B

Radical Germylzincation of α-Heteroatom-Substituted Alkynes

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