- Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral Iodane
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The first total and biomimetic synthesis of the natural bis(sesquiterpene) (-)-bacchopetiolone (revised structure) was completed through a highly diastereoselective hydroxylative phenol dearomatization/[4+2]-dimerization cascade conversion of (+)-curcuphe
- Coffinier, Romain,Assal, Mourad El,Peixoto, Philippe A.,Bosset, Cyril,Miqueu, Karinne,Sotiropoulos, Jean-Marc,Pouységu, Laurent,Quideau, Stéphane
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supporting information
p. 1120 - 1123
(2016/03/15)
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- Twist does a twist to the reactivity: Stoichiometric and catalytic oxidations with twisted tetramethyl-IBX
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The methyl groups in TetMe-IBX lower the activation energy corresponding to the rate-determining hypervalent twisting (theoretical calculations), and the steric relay between successive methyl groups twists the structure, which manifests in significant solubility in common organic solvents. Consequently, oxidations of alcohols and sulfides occur at room temperature in common organic solvents. In situ generation of the reactive TetMe-IBX from its precursor iodo-acid, i.e., 3,4,5,6-tetramethyl-2-iodobenzoic acid, in the presence of oxone as a co-oxidant facilitates the oxidation of diverse alcohols at room temperature.
- Moorthy, Jarugu Narasimha,Senapati, Kalyan,Parida, Keshaba Nanda,Jhulki, Samik,Sooraj, Kunnikuruvan,Nair, Nisanth N.
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p. 9593 - 9601
(2012/01/03)
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