98361-31-0Relevant academic research and scientific papers
Total Synthesis of Epoxyeujindole A
Lu, Zhaohong,Li, Hailong,Bian, Ming,Li, Ang
, p. 13764 - 13767 (2015)
The total synthesis of epoxyeujindole A, a structurally unusual indole diterpenoid isolated from Eupenicillium javanicum, has been accomplished for the first time. The synthesis features a late-stage cationic cyclization strategy, which took advantage of an electron-rich olefinic substrate. The CDE ring system was assembled via an enantioselective conjugate addition/alkylation, a Luche cyclization, and a Nozaki-Hiyama-Kishi reaction. The heavily substituted A ring was constructed through a Suzuki-Miyaura coupling and a cationic cyclization, and the bridged fused B ring was formed through a Prins reaction.
Total synthesis of five natural eremophilane-type sesquiterpenoids
Meng, Zhe,Liu, Bo
, p. 957 - 962 (2018/02/19)
The first total syntheses of five natural eremophilane-type sesquiterpenoids were achieved in 4-12 steps via a common synthetic intermediate. The syntheses feature a double Michael addition, Robinson annulation, α-enolization of an unsaturated ketone, and
A ring contraction strategy toward a diastereoselective total synthesis of (+)-bakkenolide A
Carneiro, Vania M. T.,Ferraz, Helena M. C.,Vieira, Tiago O.,Ishikawa, Eloisa E.,Silva Jr., Luiz F.
supporting information; experimental part, p. 2877 - 2882 (2010/08/13)
A diastereoselective route to (+)-bakkenolide A is presented from the readily available optically active Wieland-Miescher ketone. This novel synthesis of this sesquiterpene lactone features the following as key stereoselective transformations: (i) the ring contraction reaction of a octalone mediated by thallium(III) nitrate (TTN); (ii) a hydrogenation to create the cis-fused junction; and (iii) the formation of the C7 quaternary center through an enolate intermediate. Furthermore, during this work, the absolute configuration of a trinorsesquiterpene isolated from Senecio Humillimus was assigned.
Lewis Acid Catalysed Michael-type Addition. A New Regio- and Diastereoselective Annulation Method using Methyl Vinyl Ketone
Duhamel, Pierre,Dujardin, Gilles,Hennequin, Laurent,Poirier, Jean-Marie
, p. 387 - 396 (2007/10/02)
A new annulation method is presented, involving a boron trifluoride catalysed Michael addition of trialkylsilyl enol ethers to methyl vinyl ketone (MVK) in the presence of a hydroxylic compound.This methodology allows regiospecific 3-oxobutylation of eith
Efficient Trapping of Ketone Enolates with Acrylate and β-Sulfonylacrylate Thioesters, β-Sulfonyl-, β-sulfinyl- and β-Chloro-vinyl Ketones; Facile Preparation of a Hydrindanone, cis-Dimethyloctalone, and Unsaturated 1,5-Dicarbonyl Compounds
Dancer, Robert J.,Haynes, Richard K.,Laughlin, Wendy A.,Vonwiller, Simone C.
, p. 1375 - 1389 (2007/10/02)
Tandem conjugate addition-ring closure involving reaction of the lithium enolate arising from conjugate addition of lithiated (E)-but-2-enyldiphenylphosphine oxide to 2-methyl-cyclopent-2-enone with two moles of t-butylthioacrylate generates a hydrindanol
A Silyl Enol Ether Variation of the Robinson Annulation
Huffman, John W.,Potnis, Shailesh M.,Satish, Amruthur V.
, p. 4266 - 4270 (2007/10/02)
The Lewis acid catalyzed reaction of regioselectively generated silyl enol ethers with vinyl ketones has been explored as an alternative to the Robinson annulation sequence.Alkylation of the trimethylsilyl enol ethers of cyclohexanone, 2-methylcyclohexanone, and 2,3-dimethylcyclohexanone with ethyl vinyl ketone, 3-penten-2-one, and methyl vinyl ketone ethylene ketal gave a series of 1,5-diketones.Cyclization of the diketones affords 2-octalones in fair to good overall yield.This procedure has been used to prepare in good yield 5,10-dimethyl-Δ1(9)-2-octalone, an important intermediate for sesquiterpene synthesis, with a cis/trans ratio of 3 to 1.Alkylation of the trimethylsilyl enol ether of isobutyraldehyde with 3-penten-2-one, methyl vinyl ketone, and its ethylene ketal followed by cyclization affords 4,4,5-trimethyl- and 4,4-dimethyl-2-cyclohexen-1-one.This method has been employed in the synthesis of 5-(hydroxymethyl)-2,4,4-trimethyl-2-cyclohexen-1-one, a potential synthon for ring A of the taxane diterpenes.
