Total Synthesis of Mycalisine B
The first total synthesis of the marine nucleoside Mycalisine B—a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside—has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-<i>O</i>...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-04-01
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| Series: | Marine Drugs |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1660-3397/17/4/226 |
| _version_ | 1798040302349451264 |
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| author | Haixin Ding Zhizhong Ruan Peihao Kou Xiangyou Dong Jiang Bai Qiang Xiao |
| author_facet | Haixin Ding Zhizhong Ruan Peihao Kou Xiangyou Dong Jiang Bai Qiang Xiao |
| author_sort | Haixin Ding |
| collection | DOAJ |
| description | The first total synthesis of the marine nucleoside Mycalisine B—a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside—has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-<i>O</i>-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) I<sub>2</sub> catalyzed acetonide formation from 1,2,3,5-tetra-<i>O</i>-acetylribose and acetone at large scale; (2) Vorbrüggen glycosylation using <i>N</i><sup>4</sup>-benzoyl-5-cyano-6-bromo-7<i>H</i>-pyrrolo[2,3–<i>d</i>]pyrimidine as a nucleobase to avoid formation of <i>N</i>-3 isomer; (3) mild and scalable reaction conditions. |
| first_indexed | 2024-04-11T22:05:45Z |
| format | Article |
| id | doaj.art-f34e1c32b66c4adda86338e90e9fcdcb |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T22:05:45Z |
| publishDate | 2019-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-f34e1c32b66c4adda86338e90e9fcdcb2022-12-22T04:00:44ZengMDPI AGMarine Drugs1660-33972019-04-0117422610.3390/md17040226md17040226Total Synthesis of Mycalisine BHaixin Ding0Zhizhong Ruan1Peihao Kou2Xiangyou Dong3Jiang Bai4Qiang Xiao5Jiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, ChinaJiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, ChinaJiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, ChinaJiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, ChinaJiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, ChinaJiangxi Key Laboratory of Organic Chemistry, Institute of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013, ChinaThe first total synthesis of the marine nucleoside Mycalisine B—a naturally occurring and structurally distinct 4,5-unsaturated 7-deazapurine nucleoside—has been accomplished in 10 linear steps with 27.5% overall yield from commercially available 1,2,3,5-tetra-<i>O</i>-acetyl-ribose and tetracyanoethylene. Key steps of the approach include: (1) I<sub>2</sub> catalyzed acetonide formation from 1,2,3,5-tetra-<i>O</i>-acetylribose and acetone at large scale; (2) Vorbrüggen glycosylation using <i>N</i><sup>4</sup>-benzoyl-5-cyano-6-bromo-7<i>H</i>-pyrrolo[2,3–<i>d</i>]pyrimidine as a nucleobase to avoid formation of <i>N</i>-3 isomer; (3) mild and scalable reaction conditions.https://www.mdpi.com/1660-3397/17/4/226marine nucleosidetotal synthesisvorbrüggen glycosylationmycalisine B |
| spellingShingle | Haixin Ding Zhizhong Ruan Peihao Kou Xiangyou Dong Jiang Bai Qiang Xiao Total Synthesis of Mycalisine B Marine Drugs marine nucleoside total synthesis vorbrüggen glycosylation mycalisine B |
| title | Total Synthesis of Mycalisine B |
| title_full | Total Synthesis of Mycalisine B |
| title_fullStr | Total Synthesis of Mycalisine B |
| title_full_unstemmed | Total Synthesis of Mycalisine B |
| title_short | Total Synthesis of Mycalisine B |
| title_sort | total synthesis of mycalisine b |
| topic | marine nucleoside total synthesis vorbrüggen glycosylation mycalisine B |
| url | https://www.mdpi.com/1660-3397/17/4/226 |
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