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Total Synthesis of (±)-Gephyrotoxin by Amide-Selective Reductive Nucleophilic Addition
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...
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| Published in: | Angewandte Chemie International Edition 2014-01, Vol.53 (2), p.512-516 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c5475-663904bcf53c8c05b9ab1d87b910259fbdaefeff7279d18620ea696fde92e11f3 |
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| cites | cdi_FETCH-LOGICAL-c5475-663904bcf53c8c05b9ab1d87b910259fbdaefeff7279d18620ea696fde92e11f3 |
| container_end_page | 516 |
| container_issue | 2 |
| container_start_page | 512 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 53 |
| creator | Shirokane, Kenji Wada, Takamasa Yoritate, Makoto Minamikawa, Ryo Takayama, Nobuaki Sato, Takaaki Chida, Noritaka |
| description | 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 most concise and efficient total synthesis of (±)‐gephyrotoxin described to date.
Aim for selectivity: A chemoselective approach that utilizes N‐methoxyamides has been developed for the total synthesis of (±)‐gephyrotoxin. The N‐methoxy group enabled the direct coupling of the amide with an aldehyde and amide‐selective reductive allylation in the presence of a more electrophilic methyl ester, which resulted in the most concise and efficient total synthesis of (±)‐gephyrotoxin described to date. |
| doi_str_mv | 10.1002/anie.201308905 |
| format | article |
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Aim for selectivity: A chemoselective approach that utilizes N‐methoxyamides has been developed for the total synthesis of (±)‐gephyrotoxin. The N‐methoxy group enabled the direct coupling of the amide with an aldehyde and amide‐selective reductive allylation in the presence of a more electrophilic methyl ester, which resulted in the most concise and efficient total synthesis of (±)‐gephyrotoxin described to date.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201308905</identifier><identifier>PMID: 24288230</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Aldehydes ; Alkaloids - chemical synthesis ; Alkaloids - chemistry ; Amides ; Amides - chemistry ; Catalysis ; chemoselectivity ; Esters ; Functional groups ; gephyrotoxin ; Joining ; Mesylates - chemistry ; Molecular Structure ; nucleophilic addition ; Oxidation-Reduction ; Redox reactions ; Scandium - chemistry ; Stereoisomerism ; Synthesis ; total synthesis ; Trialkyltin Compounds - chemistry ; Utilization</subject><ispartof>Angewandte Chemie International Edition, 2014-01, Vol.53 (2), p.512-516</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5475-663904bcf53c8c05b9ab1d87b910259fbdaefeff7279d18620ea696fde92e11f3</citedby><cites>FETCH-LOGICAL-c5475-663904bcf53c8c05b9ab1d87b910259fbdaefeff7279d18620ea696fde92e11f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24288230$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shirokane, Kenji</creatorcontrib><creatorcontrib>Wada, Takamasa</creatorcontrib><creatorcontrib>Yoritate, Makoto</creatorcontrib><creatorcontrib>Minamikawa, Ryo</creatorcontrib><creatorcontrib>Takayama, Nobuaki</creatorcontrib><creatorcontrib>Sato, Takaaki</creatorcontrib><creatorcontrib>Chida, Noritaka</creatorcontrib><title>Total Synthesis of (±)-Gephyrotoxin by Amide-Selective Reductive Nucleophilic Addition</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>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 most concise and efficient total synthesis of (±)‐gephyrotoxin described to date.
Aim for selectivity: A chemoselective approach that utilizes N‐methoxyamides has been developed for the total synthesis of (±)‐gephyrotoxin. The N‐methoxy group enabled the direct coupling of the amide with an aldehyde and amide‐selective reductive allylation in the presence of a more electrophilic methyl ester, which resulted in the most concise and efficient total synthesis of (±)‐gephyrotoxin described to date.</description><subject>Aldehydes</subject><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - chemistry</subject><subject>Amides</subject><subject>Amides - chemistry</subject><subject>Catalysis</subject><subject>chemoselectivity</subject><subject>Esters</subject><subject>Functional groups</subject><subject>gephyrotoxin</subject><subject>Joining</subject><subject>Mesylates - chemistry</subject><subject>Molecular Structure</subject><subject>nucleophilic addition</subject><subject>Oxidation-Reduction</subject><subject>Redox reactions</subject><subject>Scandium - chemistry</subject><subject>Stereoisomerism</subject><subject>Synthesis</subject><subject>total synthesis</subject><subject>Trialkyltin Compounds - chemistry</subject><subject>Utilization</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqFkc1u1DAUhSMEoqWwZYkisSmLDNd2HMfLUVWGStXw06IuLce-1rhk4mmcQPNYvAJPhkcpI8Smq3sW3znSPSfLXhNYEAD6XnceFxQIg1oCf5IdE05JwYRgT5MuGStEzclR9iLG28TXNVTPsyNaJkUZHGc312HQbX41dcMGo495cPnp71_vihXuNlMfhnDvu7yZ8uXWWyyusEUz-B-Yf0U7zmo9mhbDbuNbb_KltX7woXuZPXO6jfjq4Z5k3z6cX599LC4_rS7OlpeF4aXgRVUxCWVjHGemNsAbqRtia9FIApRL11iNDp0TVEhL6ooC6kpWzqKkSIhjJ9npnLvrw92IcVBbHw22re4wjFERAQRkuS_kUbSUIFKVJU3o2__Q2zD2XXokUYJVpRACErWYKdOHGHt0atf7re4nRUDt11H7ddRhnWR48xA7Nlu0B_zvHAmQM_DTtzg9EqeW64vzf8OL2evjgPcHr-6_q0owwdXNeqXWXwTUjH9WwP4Acn-qKw</recordid><startdate>20140107</startdate><enddate>20140107</enddate><creator>Shirokane, Kenji</creator><creator>Wada, Takamasa</creator><creator>Yoritate, Makoto</creator><creator>Minamikawa, Ryo</creator><creator>Takayama, Nobuaki</creator><creator>Sato, Takaaki</creator><creator>Chida, Noritaka</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140107</creationdate><title>Total Synthesis of (±)-Gephyrotoxin by Amide-Selective Reductive Nucleophilic Addition</title><author>Shirokane, Kenji ; 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Aim for selectivity: A chemoselective approach that utilizes N‐methoxyamides has been developed for the total synthesis of (±)‐gephyrotoxin. The N‐methoxy group enabled the direct coupling of the amide with an aldehyde and amide‐selective reductive allylation in the presence of a more electrophilic methyl ester, which resulted in the most concise and efficient total synthesis of (±)‐gephyrotoxin described to date.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>24288230</pmid><doi>10.1002/anie.201308905</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | Aldehydes Alkaloids - chemical synthesis Alkaloids - chemistry Amides Amides - chemistry Catalysis chemoselectivity Esters Functional groups gephyrotoxin Joining Mesylates - chemistry Molecular Structure nucleophilic addition Oxidation-Reduction Redox reactions Scandium - chemistry Stereoisomerism Synthesis total synthesis Trialkyltin Compounds - chemistry Utilization |
| title | Total Synthesis of (±)-Gephyrotoxin by Amide-Selective Reductive Nucleophilic Addition |
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