- Access to orthogonal protected phenols - Synthesis of a silylated quinol
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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
- Siddiqi, Shahzad A.,Heckrodt, Thilo J.
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- A short access to the skeleton of elisabethin a and formal syntheses of elisapterosin B and colombiasin A
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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
- Preindl, Johannes,Leitner, Christian,Baldauf, Simon,Mulzer, Johann
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- Synthesis of polyfluoroalkyl aza-polycyclic aromatic hydrocarbons enabled by addition of perfluoroalkyl radicals onto vinyl azides
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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
- Wang, Yi-Feng,Lonca, Geoffroy Herve,Le Runigo, Maiwenn,Chiba, Shunsuke
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supporting information
p. 4272 - 4275
(2014/10/15)
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- Formal synthesis of (-)-kendomycin featuring a prins-cyclization to construct the macrocycle
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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
- Bahnck, Kevin B.,Rychnovsky, Scott D.
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supporting information; experimental part
p. 13177 - 13181
(2009/03/12)
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- Total synthesis of elisabethin A: Intramolecular Diels-Alder reaction under biomimetic conditions
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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
- Heckrodt, Thilo J.,Mulzer, Johann
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p. 4680 - 4681
(2007/10/03)
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- Synthesis of mimosamycin
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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.
- Kesteleyn, Bart,De Kimpe, Norbert
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p. 635 - 639
(2007/10/03)
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- Amine Addition to Unsymmetrical Benzoquinones
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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
- Luly, Jay R.,Rapoport, Henry
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p. 2745 - 2752
(2007/10/02)
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