- A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation
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A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.
- Gn?gi, Lars,Martz, Severin Vital,Meyer, Daniel,Sch?rer, Robin Marc,Renaud, Philippe
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supporting information
p. 11646 - 11649
(2019/08/30)
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- Regiocontrolled synthesis of ring-fused thieno[2,3-c]pyrazoles through 1,3-dipolar cycloaddition of nitrile imines with sulfur-based acetylenes
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1,3-Dipolar cycloadditions of C-carboxymethyl-N-arylnitrile imines with substituted acetylenes bearing thiol or sulfone groups were studied. The sulfur controls the regiochemistry of the reaction, and this protocol was applied to the synthesis of ring-fus
- Chandanshive, Jay Zumbar,Bonini, Bianca Flavia,Gentili, Denis,Fochi, Mariafrancesca,Bernardi, Luca,Franchini, Mauro Comes
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experimental part
p. 6440 - 6447
(2011/01/13)
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- Oxidative addition of Pd(0) to Ar-SO2R bonds: Heck-type reactions of sulfones
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Phenyl vinyl sulfones and sulfoxides react with Pd(OAc)2 to form styryl sulfoxides and sulfones according to the first Mizoroki-Heck reaction reported for these thio derivatives. Only sulfones are able to react by using catalytic amounts of Pd
- Ruano, Jose Luis Garcia,Aleman, Jose,Paredes, Cristina Garcia
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p. 2683 - 2686
(2007/10/03)
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- A simplified method for the preparation of ethynyl P-tolyl sulfone and ethynyl phenyl sulfone
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Silica gel mediated desilylation of aryl 2-(trimethylsilyl)ethynyl sulfones was found to greatly simplify the synthesis of the acetylenic sulfones, ethynyl p-tolyl sulfone 1 and ethynyl phenyl sulfone 2. Each were easily prepared in good yield and high purity on a multigram scale from bis(trimethylsilyl)acetylene 3.
- Chen,Trudell
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p. 3149 - 3155
(2007/10/02)
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- Sulfone reagents in organic synthesis. VI. Sulfonyl- and silyl-substituted hydrocarbons as versatile carbanion precursors in organic synthesis
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The basic organometallic chemistry of β-silyl-substituted acetylenic, vinylic and alkyl sulfones has been investigated, with attention being given to metallation, carbometallation and the chemical reduction of carbon-carbon unsaturation. 2-Trimethylsilylvinyl and 2-trimethylsilylalkyl sulfones underwent smooth and stereoselective lithiation with RLi on the carbon α to the sulfonyl group. Carbometallation of vinyl sulfones could be achieved with RMgX or LiCuR2, but acetylenic sulfones carbometallated smoothly only with LiCuR2; with RMgX or RLi, these acetylenes underwent alkyldesulfonylation. The utility in synthesis of these metallo derivatives of sulfonyl-silyl-hydrocarbons is discussed and their value in elaborating carbon skeletons is illustrated for the preparation of alkenes, allenes, carbocycles and stereo-defined vinyl sulfones.
- Eisch, John J.,Behrooz, Mohammad,Dua, Suresh K.
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p. 121 - 136
(2007/10/02)
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