Keio University · Chemistry
Professor Noritaka Chida's research laboratory specializes in the development of innovative synthetic methodologies for complex natural products, with a strong emphasis on chemoselective transformations and stereoselective synthesis. The lab focuses on designing efficient, protecting-group-minimized routes to bioactive molecules, particularly alkaloids and antibiotics, using unique reactivity patterns such as N-methoxyamide chemistry and metal-catalyzed rearrangements. Key strategies include the Overman rearrangement, Ferrier-type rearrangements, and iridium-catalyzed reductive additions, enabling concise and enantioselective total syntheses. The work consistently emphasizes functional group tolerance and atom economy, contributing significantly to synthetic organic chemistry and drug discovery.
Figures are computed from collected data and may differ slightly.
A chemoselective approach for the total synthesis of (±)-gephyrotoxin has been developed. The key to success was the utilization of N-methoxyamides, which enabled the direct coupling of the amide with an aldehyde and selective reductive nucleophilic addition to the amide in the presence of a variety of sensitive and electrophilic functional groups, such as a methyl ester. This chemoselective approach minimized the use of protecting-group manipulations and redox reactions, which resulted in the m
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTotal synthesis of antibiotic hygromycin ANoritaka Chida, Masami Ohtsuka, Keiichi Nakazawa, and Seiichiro OgawaCite this: J. Org. Chem. 1991, 56, 9, 2976–2983Publication Date (Print):April 1, 1991Publication History Published online1 May 2002Published inissue 1 April 1991https://pubs.acs.org/doi/10.1021/jo00009a009https://doi.org/10.1021/jo00009a009research-articleACS PublicationsRequest reuse permissionsArticle Views977Altmetric-Citations81LEARN ABOUT
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTotal synthesis of (+)-lycoricidine and its 2-epimer from D-glucoseNoritaka Chida, Masami Ohtsuka, and Seiichiro OgawaCite this: J. Org. Chem. 1993, 58, 16, 4441–4447Publication Date (Print):July 1, 1993Publication History Published online1 May 2002Published inissue 1 July 1993https://pubs.acs.org/doi/10.1021/jo00068a045https://doi.org/10.1021/jo00068a045research-articleACS PublicationsRequest reuse permissionsArticle Views1075Altmetric-Citations77LEAR
Abstract Conversion of hex-5-enopyranosides into substituted cyclohexanones (Ferrier rearrangement) was found to proceed efficiently with a catalytic amount of various mercury(II) salts at room temperature in a neutral solvent system. Among the mercury(II) salts tested, mercury(II) trifluoroacetate showed the highest activity. Four optically active cyclohexenones were prepared from hex-5-enopyranosides utilizing this method.
The chiral and stereoselective synthesis of (+)-lactacystin 1, the first non-protein neurotrophic factor, is described; the γ-lactam portion possessing a quaternary carbon in 1 was constructed stereoselectively from D-glucose using the allylic trichloroacetimidate rearrangement (Overman rearrangement) as the key reaction.
An iridium-catalyzed reductive nucleophilic addition to secondary amides is reported. After the iridium-catalyzed reduction, the resulting imines can undergo the Strecker reaction, the Mannich reaction, allylation, and [3 + 2]-cycloaddition. The method shows high chemoselectivity in the presence of other functional groups such as methyl ester.
An approach to cyclic nitrones from N-hydroxylactam derivatives is documented. The nucleophilic addition of an organolithium reagent to an N-OSEM [SEM=2-(trimethylsilyl)ethoxymethyl] lactam forms a five-membered chelated intermediate, which undergoes both elimination and deprotection to give a fully substituted nitrone in a one-pot process. When combined with the N-oxidation of easily available chiral lactams, this method becomes especially useful for the quick synthesis of chiral nitrones in en
The total synthesis of the antifungal antibiotic, polyoxin J 1 starting from myo-inositol is described; the two key components, 2 and 3, were prepared from a pair of optically resolved myo-inositol derivatives 4L and 4D, respectively, using a highly regioselective Baeyer–Villiger reaction, and finally coupled to complete the total synthesis.
The chiral and stereoselective synthesis of antimitotic phenanthridone alkaloids, (+)-7-deoxypancratistatin (1) and (+)-7-deoxytrans-dihydronarciclasine (2) is described.Both natural products were synthesized from the common compound (4), which had been prepared from D-glucose and employed for the synthesis of lycoricidine (3).The highly oxygenated phenanthridone alkaloids,l represented by pancratistatin?a7-deoxypancratistatin(1),2b 7-deoxy-trans-dihydronarciclasine (t)?c and lycoricidine (3)2d
A chirality transfer approach using acyclic polyol intermediates for the synthesis of (+)-neostenine (1) has been developed. The sequential Overman/Claisen rearrangement of an allylic 1,2-diol was especially useful, installing two contiguous stereocenters with complete diastereoselectivity in a one-pot sequence. The SmI<sub>2</sub> -mediated cyclization and the subsequent chemoselective reduction of a lactam moiety accomplished the first enantioselective total synthesis of (+)-neostenine (1).
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