Tohoku University · Chemistry
Professor Yoshiharu Iwabuchi's research lab specializes in the development of innovative organic synthesis methodologies, with a strong focus on enantioselective transformations and total synthesis of bioactive natural products. The lab pioneers catalytic asymmetric reactions—such as the Baylis-Hillman and Morita-Baylis-Hillman reactions—using chiral catalysts like cinchona alkaloids and rhodium-nitrenoid species to construct complex molecular architectures with high stereocontrol. Key research directions include the synthesis of immunosuppressants, antitumor agents, and other medicinally relevant compounds, often involving novel cyclization and oxidation strategies. The lab also explores the application of stable nitroxyl radicals, such as TEMPO, for selective oxidation processes in complex molecule synthesis.
Figures are computed from collected data and may differ slightly.
A new enantiocontrolled synthesis of a potent immunosuppressant(-)-mycestericin E has been accomplished by using cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction of an aldehyde with 1,1,1,3,3,3-hexafluoroisopropyl acrylate and Lewis acid-promoted cyclisation of an epoxytrichloroacetimidate as the key steps.
The oxidation of primary and secondary alcohols to the corresponding aldehydes (or carboxylic acids) or ketones is a fundamental transformation in organic synthesis. Stable organic nitroxyl radicals as represented by 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) (1) have been used extensively to catalyze the oxidation of a number of alcohol substrates employing environmentally benign co-oxidants such as bleach (NaOCl) or PhI(OAc)2. Although TEMPO oxidation is better known as a method for selectiv
A versatile, highly enantiocontrolled entry to the spiro-beta-lactam core of chartellines has been developed by expanding the scope of oxidative nitrogen atom transfer methodology based on chiral Rh-nitrenoid species.
Herein, we describe the first asymmetric total synthesis of (-)-martinelline ((-)-2) and the second total synthesis of (-)-martinellic acid ((-)-1) by employing a tandem Mukaiyama-Mannich reaction/aminal cyclization as the key step.
The Morita-Baylis-Hillman reaction, α-hydroxyalkylation of activated olefins, has attracted considerable research interest because of the synthetic utility of the densely functionalized product as well as the exquisite tandem Michael-aldol reaction process under nucleophilic catalysis. This review gives an overview on recent remarkable progress in the Morita-Baylis-Hillman reactions. Several other successful methods affording the Morita-Baylis-Hillman type adducts are also reviewed by focusing t
The 1,5-diaryl-3-oxo-1,4-pentadiene analogs can yield good lead compounds for cancer chemotherapy, to overcome low bioavailability of curcumin.
We have recently disclosed that a less hindered class of nitroxyl radicals, i.e., 2-azaadamantan-N-oxyl (AZADO), 1-Me-AZADO, and 9-azabicyclo[3.3.1]nonan-N-oxyl (ABNO), exhibit marked catalytic activity for the oxidation of alcohols with the aid of environmentally friendly oxidants, offering a green and sustainable option for current alcohol oxidation. Encouraged by their outstanding catalytic performance, we envisioned the development of scalable routes to these radicals that could be extended
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