98361-31-0Relevant articles and documents
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.
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.
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
