118598-22-4Relevant academic research and scientific papers
Synthesis of 7-Membered Ring Carbocycles via a Palladium-Catalyzed Intramolecular Allylic Alkylation–Isomerization–Cope Rearrangement Cascade
Tsuruda, Kazuki,Tokumoto, Takahisa,Inoue, Naoya,Nakajima, Masaya,Nemoto, Tetsuhiro
supporting information, p. 2836 - 2840 (2018/06/21)
We developed a novel method for synthesizing seven-membered ring carbocycles via a palladium-catalyzed intramolecular allylic alkylation–isomerization–Cope rearrangement cascade. Using easily available lactone derivatives as substrates, the target cascade
New dimerization and cascade oligomerization reactions of dimethyl 2-phenylcyclopropan-1,1-dicarboxylate catalyzed by Lewis acids
Novikov, Roman A.,Korolev, Victor A.,Timofeev, Vladimir P.,Tomilov, Yury V.
scheme or table, p. 4996 - 4999 (2011/10/08)
New routes to transform donor-acceptor cyclopropanes in the presence of Lewis acids have been found. The reaction of dimethyl 2-phenylcyclopropan-1,1- dicarboxylate, a typical representative of this class of compounds, with an equimolar amount of anhydrou
Lewis acid-catalyzed isomerization of 2-arylcyclopropane-1,1- dicarboxylates: A new efficient route to 2-styrylmalonates
Chagarovskiy, Alexey O.,Ivanova, Olga A.,Rakhmankulov, Eduard R.,Budynina, Ekaterina M.,Trushkov, Igor V.,Melnikov, Mikhail Ya.
supporting information; experimental part, p. 3179 - 3184 (2011/02/22)
A facile efficient approach to the 2-styrylmalonates via the Lewis acid-catalyzed isomerization of 2-arylcyclopropane-1,1-dicarboxylates has been developed. The efficiency of this method was demonstrated for a representative series of such cyclopropanes.
A Short, Oxetane-Based Synthesis of (+/-)-Sarracenin
Hoye, Thomas R.,Richardson, Wendy S.
, p. 688 - 693 (2007/10/02)
(+/-)-Sarracenin (1) was synthesized in nine steps and six pots from simple precursors acetaldehyde and cyclopentadiene.Paterno-Buechi photocycloaddition of this pair yielded two diastereomeric oxetanes (3x, 3n).The major, exo isomer underwent highly regioselective acid-catalyzed methanolysis at the methyl-bearing oxetane center to give a 3-cyclopentenol derivative (8).Attachment of a methyl 2-(2-phenylethenyl)ethanoate moiety, a 3-oxopropanoate equivalent, with inversion of the toluenesulfonate 9 derived from 8 gave a diene (11) containing all of the necessary carbon atoms.Following decarbomethoxylation, both olefins were simultaneously ozonized to an in situ equivalent of trialdehyde (2) which has played a role in previous synthetic studies and biosynthetic postulates in this area.Spontaneous dehydration of 2 produced (+/-)-sarracenin in 18percent overall yield from the tosylate 9, the first purified intermediate in the sequence.
