virginiamycin and crotylsilane

virginiamycin has been researched along with crotylsilane* in 1 studies

Other Studies

1 other study(ies) available for virginiamycin and crotylsilane

Article	Year
Total synthesis of (-)-virginiamycin M2: application of crotylsilanes accessed by enantioselective Rh(II) or Cu(I) promoted carbenoid Si-H insertion. The Journal of organic chemistry, 2011, Dec-16, Volume: 76, Issue:24 A stereoselective synthesis of the antibiotic (-)-virginiamycin M(2) is detailed. A convergent strategy was utilized that proceeded in 10 steps (longest linear sequence) from enantioenriched silane (S)-15. This reagent, which was prepared via a Rh(II)- or Cu(I)-catalyzed carbenoid Si-H insertion, was used to introduce the desired olefin geometry and stereocenters of the C1-C5 propionate subunit. A modified Negishi cross-coupling or an efficient alkoxide-directed titanium-mediated alkyne-alkyne reductive coupling strategy was utilized to assemble the trisubstituted (E,E)-diene. An underutilized late-stage SmI(2)-mediated macrocyclization was employed to construct the 23-membered macrocycle scaffold of the natural product. Topics: Alkenes; Alkynes; Anti-Bacterial Agents; Catalysis; Chromatography, High Pressure Liquid; Copper; Cyclization; Humans; Hydrogen; Magnetic Resonance Spectroscopy; Molecular Structure; Oxidation-Reduction; Rhodium; Silanes; Silicon; Stereoisomerism; Virginiamycin	2011

Article

Year

Total synthesis of (-)-virginiamycin M2: application of crotylsilanes accessed by enantioselective Rh(II) or Cu(I) promoted carbenoid Si-H insertion.

The Journal of organic chemistry, 2011, Dec-16, Volume: 76, Issue:24

A stereoselective synthesis of the antibiotic (-)-virginiamycin M(2) is detailed. A convergent strategy was utilized that proceeded in 10 steps (longest linear sequence) from enantioenriched silane (S)-15. This reagent, which was prepared via a Rh(II)- or Cu(I)-catalyzed carbenoid Si-H insertion, was used to introduce the desired olefin geometry and stereocenters of the C1-C5 propionate subunit. A modified Negishi cross-coupling or an efficient alkoxide-directed titanium-mediated alkyne-alkyne reductive coupling strategy was utilized to assemble the trisubstituted (E,E)-diene. An underutilized late-stage SmI(2)-mediated macrocyclization was employed to construct the 23-membered macrocycle scaffold of the natural product.

Topics: Alkenes; Alkynes; Anti-Bacterial Agents; Catalysis; Chromatography, High Pressure Liquid; Copper; Cyclization; Humans; Hydrogen; Magnetic Resonance Spectroscopy; Molecular Structure; Oxidation-Reduction; Rhodium; Silanes; Silicon; Stereoisomerism; Virginiamycin

2011