1760-80-1Relevant academic research and scientific papers
Access to orthogonal protected phenols - Synthesis of a silylated quinol
Siddiqi, Shahzad A.,Heckrodt, Thilo J.
, p. 328 - 331 (2003)
Herein we describe the synthesis of t-butyldimethylsilyl protected quinol (9), using an oxidation/reduction sequence to create the desired orthogonality. The title compound acts as a synthetic equivalent for a quinone, required in the total synthesis of E
A short access to the skeleton of elisabethin a and formal syntheses of elisapterosin B and colombiasin A
Preindl, Johannes,Leitner, Christian,Baldauf, Simon,Mulzer, Johann
, p. 4276 - 4279 (2014)
A short stereoselective synthesis of the Elisabethin A skeleton 4 is described, which opens a formal access to the diterpenes Elisapterosin B and Colombiasin A as well. Key reactions were an intermolecular endo-selective Diels-Alder reaction to generate t
Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
Wang, Yi-Feng,Lonca, Geoffroy Herve,Le Runigo, Maiwenn,Chiba, Shunsuke
supporting information, p. 4272 - 4275 (2014/10/15)
Radical perfluoroalkylation of α-(biaryl-2-yl)vinyl azides is capable of supplying polyfluoroalkyl aza-polycyclic aromatic hydrocarbons (aza-PAHs). Commercially available Me3SiRf (Rf = CF 3, C2F5
Formal synthesis of (-)-kendomycin featuring a prins-cyclization to construct the macrocycle
Bahnck, Kevin B.,Rychnovsky, Scott D.
supporting information; experimental part, p. 13177 - 13181 (2009/03/12)
The kendomycin skeleton was prepared by a highly convergent strategy in which the benzofuran fragment and the acyclic iodide fragment were prepared by standard methods and joined using a Suzuki coupling. The distinctive reaction in our approach was an int
Total synthesis of elisabethin A: Intramolecular Diels-Alder reaction under biomimetic conditions
Heckrodt, Thilo J.,Mulzer, Johann
, p. 4680 - 4681 (2007/10/03)
We describe the first total synthesis of the marine diterpenoid elisabethin A. The synthesis uses (S)-hydroxy-2-methyl-propionate as the chiral starting material, which is elaborated into a dienyl-iodide and added to an aryl acetic acid ester via enolate
Synthesis of mimosamycin
Kesteleyn, Bart,De Kimpe, Norbert
, p. 635 - 639 (2007/10/03)
Mimosamycin (1) was synthesized in eight steps with an overall yield of 13% from 2-methoxy-3-methyl-1,4-benzoquinone by regioselective introduction of a chloromethyl group at C-6 and a methoxycarbonylmethyl group at C-5 and subsequent reaction of the intermediate methyl (o- (chloromethyl)phenyl)acetate derivative 16 with methylamine. Oxidation of the 5,7,8-trimethoxy-2,6-dimethyl-1,4-dihydroisoquinoline-3(2H)-one 17 thus obtained, using cerium(IV) ammonium nitrate as a selective oxidizing agent, gave mimosamycin (1) in good overall yield.
Amine Addition to Unsymmetrical Benzoquinones
Luly, Jay R.,Rapoport, Henry
, p. 2745 - 2752 (2007/10/02)
New routes to 2-methoxy-3-methyl-1,4-benzoquinone and 4-methoxy-3-methyl-1,2-benzoquinone have been developed.Both quinones undergo highly regioselective oxidative amination with pyrrolidine and copper acetate, yielding aminoquinones related to the mitomy
