Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-one
This study describes an attempt to develop a synthetic route using theoretical calculations, i.e., in silico synthesis route development. The KOSP program created four potential synthetic routes for generating 2,6-dimethylchroman-4-one. In silico screening of these four synthetic routes was then per...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2010-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/15/11/8289/ |
| _version_ | 1819033054552784896 |
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| author | Hidetoshi Yamamoto Michinori Sumimoto Takaaki Kuroda Kenji Hori Hirotaka Sadatomi Atsuo Miyamoto |
| author_facet | Hidetoshi Yamamoto Michinori Sumimoto Takaaki Kuroda Kenji Hori Hirotaka Sadatomi Atsuo Miyamoto |
| author_sort | Hidetoshi Yamamoto |
| collection | DOAJ |
| description | This study describes an attempt to develop a synthetic route using theoretical calculations, i.e., in silico synthesis route development. The KOSP program created four potential synthetic routes for generating 2,6-dimethylchroman-4-one. In silico screening of these four synthetic routes was then performed. In silico screening involves theoretical analysis of synthetic routes prior to actual experimental work. A synthetic route using the Mitsunobu reaction had already been reported by Hoddgets et al. Theoretical investigations were also conducted on two SNAr reactions as well as a Michael reaction before they were examined experimentally. In silico screening using DFT calculations indicated that only the Michael reaction was likely to produce the target. Experimental work confirmed that the target was obtained in a yield of 76.4% using the Michael reaction. The other two routes, except for the Mitsunobu reaction, failed to generate the target. Our results demonstrate that theoretical calculations can be used to narrow down the number of experiments that need to be conducted when developing novel synthetic routes. |
| first_indexed | 2024-12-21T07:11:44Z |
| format | Article |
| id | doaj.art-e7ca4912f30e44d8a62ef716bb997953 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T07:11:44Z |
| publishDate | 2010-11-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-e7ca4912f30e44d8a62ef716bb9979532022-12-21T19:11:58ZengMDPI AGMolecules1420-30492010-11-0115118289830410.3390/molecules15118289Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-oneHidetoshi YamamotoMichinori SumimotoTakaaki KurodaKenji HoriHirotaka SadatomiAtsuo MiyamotoThis study describes an attempt to develop a synthetic route using theoretical calculations, i.e., in silico synthesis route development. The KOSP program created four potential synthetic routes for generating 2,6-dimethylchroman-4-one. In silico screening of these four synthetic routes was then performed. In silico screening involves theoretical analysis of synthetic routes prior to actual experimental work. A synthetic route using the Mitsunobu reaction had already been reported by Hoddgets et al. Theoretical investigations were also conducted on two SNAr reactions as well as a Michael reaction before they were examined experimentally. In silico screening using DFT calculations indicated that only the Michael reaction was likely to produce the target. Experimental work confirmed that the target was obtained in a yield of 76.4% using the Michael reaction. The other two routes, except for the Mitsunobu reaction, failed to generate the target. Our results demonstrate that theoretical calculations can be used to narrow down the number of experiments that need to be conducted when developing novel synthetic routes.http://www.mdpi.com/1420-3049/15/11/8289/In silico screeningsynthetic route developmenttheoretical calculationsMitsunobu reactionMichael reaction |
| spellingShingle | Hidetoshi Yamamoto Michinori Sumimoto Takaaki Kuroda Kenji Hori Hirotaka Sadatomi Atsuo Miyamoto Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-one Molecules In silico screening synthetic route development theoretical calculations Mitsunobu reaction Michael reaction |
| title | Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-one |
| title_full | Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-one |
| title_fullStr | Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-one |
| title_full_unstemmed | Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-one |
| title_short | Towards the Development of Synthetic Routes Using Theoretical Calculations: An Application of In Silico Screening to 2,6-Dimethylchroman-4-one |
| title_sort | towards the development of synthetic routes using theoretical calculations an application of in silico screening to 2 6 dimethylchroman 4 one |
| topic | In silico screening synthetic route development theoretical calculations Mitsunobu reaction Michael reaction |
| url | http://www.mdpi.com/1420-3049/15/11/8289/ |
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