Critical Switching of Cyclization Modes of Polyepoxides in Acidic Aqueous Media and Neutral Water: Synthesis and Revised Structure of a Nerolidol‐Type Sesquiterpenoid
Biomimetic epoxide‐opening cascades of polyepoxides enable the efficient and rapid construction of polyether frameworks. Herein, we show that the epoxide‐opening cascade cyclization that affords tetrahydrofuran products in acidic aqueous media produces tetrahydropyran (THP) in neutral water. THP for...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2019-07, Vol.58 (30), p.10168-10172 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Nishikawa, Keisuke Morita, Kengo Hashimoto, Subaru Hoshino, Akihiro Ikeuchi, Takumi Kumagai, Momochika Morimoto, Yoshiki |
| description | Biomimetic epoxide‐opening cascades of polyepoxides enable the efficient and rapid construction of polyether frameworks. Herein, we show that the epoxide‐opening cascade cyclization that affords tetrahydrofuran products in acidic aqueous media produces tetrahydropyran (THP) in neutral water. THP formation proceeded by simply heating polyepoxides in neutral water and followed a different cyclization mode from those observed so far. The novel cascade cyclization in H2O was applied to the synthesis of a new nerolidol‐type sesquiterpenoid, resulting in revision of the proposed structure and determination of the absolute configuration.
The epoxide‐opening cascade cyclization of polyepoxides affords tetrahydrofuran (THF) products in acidic aqueous media and tetrahydropyran (THP) in neutral water. THP formation proceeded by simply heating polyepoxides in neutral water and followed a different cyclization mode from those observed so far. |
| doi_str_mv | 10.1002/anie.201906039 |
| format | Article |
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The epoxide‐opening cascade cyclization of polyepoxides affords tetrahydrofuran (THF) products in acidic aqueous media and tetrahydropyran (THP) in neutral water. THP formation proceeded by simply heating polyepoxides in neutral water and followed a different cyclization mode from those observed so far.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201906039</identifier><identifier>PMID: 31211481</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Absolute configuration ; Aqueous solutions ; biomimetic synthesis ; Biomimetics ; Cascades ; cyclization ; diastereoselectivity ; natural products ; Nerolidol ; Synthesis ; terpenoids ; Tetrahydrofuran</subject><ispartof>Angewandte Chemie International Edition, 2019-07, Vol.58 (30), p.10168-10172</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4769-2d415657d86733c25b741ea06724562a5014f67ce84254e110a5ac62b7a166713</citedby><cites>FETCH-LOGICAL-c4769-2d415657d86733c25b741ea06724562a5014f67ce84254e110a5ac62b7a166713</cites><orcidid>0000-0002-3170-8023 ; 0000-0002-4770-3091</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201906039$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201906039$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31211481$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nishikawa, Keisuke</creatorcontrib><creatorcontrib>Morita, Kengo</creatorcontrib><creatorcontrib>Hashimoto, Subaru</creatorcontrib><creatorcontrib>Hoshino, Akihiro</creatorcontrib><creatorcontrib>Ikeuchi, Takumi</creatorcontrib><creatorcontrib>Kumagai, Momochika</creatorcontrib><creatorcontrib>Morimoto, Yoshiki</creatorcontrib><title>Critical Switching of Cyclization Modes of Polyepoxides in Acidic Aqueous Media and Neutral Water: Synthesis and Revised Structure of a Nerolidol‐Type Sesquiterpenoid</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>Biomimetic epoxide‐opening cascades of polyepoxides enable the efficient and rapid construction of polyether frameworks. Herein, we show that the epoxide‐opening cascade cyclization that affords tetrahydrofuran products in acidic aqueous media produces tetrahydropyran (THP) in neutral water. THP formation proceeded by simply heating polyepoxides in neutral water and followed a different cyclization mode from those observed so far. The novel cascade cyclization in H2O was applied to the synthesis of a new nerolidol‐type sesquiterpenoid, resulting in revision of the proposed structure and determination of the absolute configuration.
The epoxide‐opening cascade cyclization of polyepoxides affords tetrahydrofuran (THF) products in acidic aqueous media and tetrahydropyran (THP) in neutral water. THP formation proceeded by simply heating polyepoxides in neutral water and followed a different cyclization mode from those observed so far.</description><subject>Absolute configuration</subject><subject>Aqueous solutions</subject><subject>biomimetic synthesis</subject><subject>Biomimetics</subject><subject>Cascades</subject><subject>cyclization</subject><subject>diastereoselectivity</subject><subject>natural products</subject><subject>Nerolidol</subject><subject>Synthesis</subject><subject>terpenoids</subject><subject>Tetrahydrofuran</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkc1u1DAQxyMEoqVw5Ygscekli7-d5bZaFajUD8QWcYy89iydKhundkIJJx6Bx-C5eBKcbikSF04ee37zk0f_onjO6IxRyl_ZFmHGKZtTTcX8QbHPFGelMEY8zLUUojSVYnvFk5SuMl9VVD8u9gTjjMmK7Rc_lxF7dLYhqxvs3SW2n0nYkOXoGvxmewwtOQ0e0vT4PjQjdOErTndsycKhR0cW1wOEIZFT8GiJbT05g6GPWfnJ9hBfk9XY9peQMN02P8AXTODJqo-D64cIk9rmmRga9KH59f3HxdgBWUG6HjALOmgD-qfFo41tEjy7Ow-Kj2-OLpbvypPzt8fLxUnppNHzknvJlFbGV9oI4bhaG8nAUm24VJpbRZncaOOgklxJYIxaZZ3ma2OZ1oaJg-Jw5-1iyIulvt5ictA0tp22rDmXvBKcqSqjL_9Br8IQ2_y7TKlKzzkTPFOzHeViSCnCpu4ibm0ca0brKcN6yrC-zzAPvLjTDust-Hv8T2gZmO-AG2xg_I-uXpwdH_2V_wZZOaoA</recordid><startdate>20190722</startdate><enddate>20190722</enddate><creator>Nishikawa, Keisuke</creator><creator>Morita, Kengo</creator><creator>Hashimoto, Subaru</creator><creator>Hoshino, Akihiro</creator><creator>Ikeuchi, Takumi</creator><creator>Kumagai, Momochika</creator><creator>Morimoto, Yoshiki</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3170-8023</orcidid><orcidid>https://orcid.org/0000-0002-4770-3091</orcidid></search><sort><creationdate>20190722</creationdate><title>Critical Switching of Cyclization Modes of Polyepoxides in Acidic Aqueous Media and Neutral Water: Synthesis and Revised Structure of a Nerolidol‐Type Sesquiterpenoid</title><author>Nishikawa, Keisuke ; Morita, Kengo ; Hashimoto, Subaru ; Hoshino, Akihiro ; Ikeuchi, Takumi ; Kumagai, Momochika ; Morimoto, Yoshiki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4769-2d415657d86733c25b741ea06724562a5014f67ce84254e110a5ac62b7a166713</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Absolute configuration</topic><topic>Aqueous solutions</topic><topic>biomimetic synthesis</topic><topic>Biomimetics</topic><topic>Cascades</topic><topic>cyclization</topic><topic>diastereoselectivity</topic><topic>natural products</topic><topic>Nerolidol</topic><topic>Synthesis</topic><topic>terpenoids</topic><topic>Tetrahydrofuran</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nishikawa, Keisuke</creatorcontrib><creatorcontrib>Morita, Kengo</creatorcontrib><creatorcontrib>Hashimoto, Subaru</creatorcontrib><creatorcontrib>Hoshino, Akihiro</creatorcontrib><creatorcontrib>Ikeuchi, Takumi</creatorcontrib><creatorcontrib>Kumagai, Momochika</creatorcontrib><creatorcontrib>Morimoto, Yoshiki</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Nishikawa, Keisuke</au><au>Morita, Kengo</au><au>Hashimoto, Subaru</au><au>Hoshino, Akihiro</au><au>Ikeuchi, Takumi</au><au>Kumagai, Momochika</au><au>Morimoto, Yoshiki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Critical Switching of Cyclization Modes of Polyepoxides in Acidic Aqueous Media and Neutral Water: Synthesis and Revised Structure of a Nerolidol‐Type Sesquiterpenoid</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2019-07-22</date><risdate>2019</risdate><volume>58</volume><issue>30</issue><spage>10168</spage><epage>10172</epage><pages>10168-10172</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Biomimetic epoxide‐opening cascades of polyepoxides enable the efficient and rapid construction of polyether frameworks. Herein, we show that the epoxide‐opening cascade cyclization that affords tetrahydrofuran products in acidic aqueous media produces tetrahydropyran (THP) in neutral water. THP formation proceeded by simply heating polyepoxides in neutral water and followed a different cyclization mode from those observed so far. The novel cascade cyclization in H2O was applied to the synthesis of a new nerolidol‐type sesquiterpenoid, resulting in revision of the proposed structure and determination of the absolute configuration.
The epoxide‐opening cascade cyclization of polyepoxides affords tetrahydrofuran (THF) products in acidic aqueous media and tetrahydropyran (THP) in neutral water. THP formation proceeded by simply heating polyepoxides in neutral water and followed a different cyclization mode from those observed so far.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31211481</pmid><doi>10.1002/anie.201906039</doi><tpages>5</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-3170-8023</orcidid><orcidid>https://orcid.org/0000-0002-4770-3091</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Absolute configuration Aqueous solutions biomimetic synthesis Biomimetics Cascades cyclization diastereoselectivity natural products Nerolidol Synthesis terpenoids Tetrahydrofuran |
| title | Critical Switching of Cyclization Modes of Polyepoxides in Acidic Aqueous Media and Neutral Water: Synthesis and Revised Structure of a Nerolidol‐Type Sesquiterpenoid |
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