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Bogonda, Ganganna,Kim, Hun Young,Oh, Kyungsoo American Chemical Society 2018 ORGANIC LETTERS Vol.20 No.9
<P>A direct acyl radical addition to 2<I>H</I>-indazoles has been achieved for the first time, where the less-aromatic <I>quinonoid</I> 2<I>H</I>-indazoles readily accepted radical species to the C-3 position. Motivated by the lack of direct acylation strategy for 2<I>H</I>-indazoles, the current method utilizes the radical acceptability of 2<I>H</I>-indazoles, discovering an ambient temperature reaction to provide facile access to a diverse array of 3-acyl-2<I>H</I>-indazoles with three points of structural diversification in 25%-83% yields.</P> [FIG OMISSION]</BR>
Scalable synthesis of the C14–C23 fragment of Eribulin and Halichondrin B
Kim U Bin,Samala Srinivas,Kim Namhyeon,Bogonda Ganganna,Lago‐Santomé Hugo,Jeong Youngdo,Kim Jin,Jung Jaehun,Jeon Sung‐Hyun,Lee Seung Jong,신현석 대한화학회 2022 Bulletin of the Korean Chemical Society Vol.43 No.12
A novel, scalable approach to the C14–C23 fragment of eribulin mesylate is disclosed. Key 2,3-Wittig rearrangement is strategically effected via [Rh] mediated decomposition of 1,2,3-triazole intermediate to derive the 2,5-trans-tetrahydrofuran motif, enabling multi-kilogram access to the desired C14–C23 fragment.
Lee, Ji Hyun,Park, Han Na,Ganganna, Bogonda,Jeong, Ji Hye,Park, Sung-Kwan,Lee, Jongkook,Baek, Sun Young Informa UK (TaylorFrancis) 2016 Food additives & contaminants. Part A. Chemistry, Vol.33 No.6
<P>A newtadalafil analoguewas found, alongwith nortadalafil, using HPLC-DAD during the inspection of a health product sold without official approval. The analogue was separated using a semi-preparative HPLC system and its structure was determined by a combination of mass spectrometry and NMR spectroscopy. The compound was identified as a tadalafil analogue in which the N-methyl group of tadalafil was replaced with a tadalafil precursor moiety. Nuclear Overhauser effect spectroscopy experiments suggested a cis-relationship between the substituents on a piperidine ring in the tadalafilmoiety.</P>
Lee, Ji Hyun,Park, Han Na,Kim, Nam Sook,Park, Seongsoo,Bogonda, Ganganna,Oh, Kyungsoo,Kang, Hoil Elsevier Sequoia 2019 Forensic science international Vol.303 No.-
<P><B>Abstract</B></P> <P>With the increasing prevalence of obesity, the use of counterfeit drugs for weight loss is widespread owing to their easy and rapid availability. Since counterfeit weight-loss drugs are not prepared under the rigorous standard of Good Manufacturing Practice (GMP), they pose a risk to public health and cause significant side effects. To counteract the risk posed by counterfeit drugs, we investigated counterfeit weight-loss drugs seized by the Incheon Customs Services using UHPLC-PDA. Five of 23 confiscated samples with distinctive pink-coloured coating contained levothyroxine, sennoside A and B, and phenolphthalein in amounts ranging from 0.03–132.40 mg/g. In addition, three unknown compounds in one of the adulterated samples containing phenolphthalein were structurally elucidated by several analytical techniques. Their accurate masses corresponded to molecular formula of C<SUB>34</SUB>H<SUB>22</SUB>O<SUB>7</SUB>, C<SUB>34</SUB>H<SUB>20</SUB>O<SUB>6</SUB>, and C<SUB>20</SUB>H<SUB>12</SUB>O<SUB>3</SUB>, respectively. These compounds were identified as impurities, possibly produced during the synthesis of phenolphthalein or by improper removal during purification. These impurities were detected for the first time in counterfeit drugs.</P> <P><B>Highlights</B></P> <P> <UL> <LI> The 23 counterfeit weight-loss drugs were screened by UHPLC-PDA analysis. </LI> <LI> Five of samples were detected in range of 0.03–132.40 mg/g. </LI> <LI> Three unknown compounds in one sample were structurally elucidated by LC-HR–MS and NMR. </LI> <LI> They were first detected in counterfeit drugs and identified as phenolphthalein impurities. </LI> <LI> These impurities were possibly produced during the synthesis of phenolphthalein. </LI> </UL> </P>
Samala, Mallesham,Lu, Thien Nhan,Mandava, Suresh,Hwang, Jungjoong,Bogonda, Ganganna,Kim, Donghoon,Park, Haeil,Kim, Deukjoon,Lee, Jongkook American Chemical Society 2018 ORGANIC LETTERS Vol.20 No.20
<P>A stereoselective protection-free asymmetric total synthesis of (+)-chamuvarinin (<B>1</B>), a potent anticancer and antitrypanosomal agent, has been accomplished. The adjacently linked [bis(tetrahydrofuran)]tetrahydropyran (THF-THF-THP) core of this natural product with seven stereogenic centers was constructed in a completely substrate-controlled fashion. The inter-ring stereochemistry (<I>threo,threo,threo</I>) of the oxatricyclic core was established in a stereoselective fashion by a chelation-controlled Keck allylation, whereas the intraring <I>cis</I> or <I>trans</I> relative stereochemistry was controlled by a stereoselective internal alkylation.</P> [FIG OMISSION]</BR>