Total Synthesis of Mycalolides A and B through Olefin Metathesis
An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1–C19 trisoxazole and C20–C35 side‐chain segments through the use of olefin metathesis and esterification as well as Julia–Ko...
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| Veröffentlicht in: | Angewandte Chemie 2015-11, Vol.127 (47), p.14380-14384 |
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| container_end_page | 14384 |
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| container_issue | 47 |
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| container_title | Angewandte Chemie |
| container_volume | 127 |
| creator | Kita, Masaki Oka, Hirotaka Usui, Akihiro Ishitsuka, Tomoya Mogi, Yuzo Watanabe, Hidekazu Tsunoda, Masaki Kigoshi, Hideo |
| description | An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1–C19 trisoxazole and C20–C35 side‐chain segments through the use of olefin metathesis and esterification as well as Julia–Kocienski olefination and enamide formation as key steps.
Von Anfang an: Eine asymmetrische Totalsynthese der Trisoxazol‐Makrolide Mycalolid A und B beruht auf dem konvergenten Aufbau des Trisoxazolmotivs C1–C19 und des Seitenkettensegments C20–C35 mit Olefinmetathese und Veresterung als Schlüsselschritten. |
| doi_str_mv | 10.1002/ange.201507795 |
| format | Article |
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Von Anfang an: Eine asymmetrische Totalsynthese der Trisoxazol‐Makrolide Mycalolid A und B beruht auf dem konvergenten Aufbau des Trisoxazolmotivs C1–C19 und des Seitenkettensegments C20–C35 mit Olefinmetathese und Veresterung als Schlüsselschritten.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201507795</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag</publisher><subject>Assembly ; Asymmetry ; Chemistry ; Decomposition reactions ; Esterification ; Formations ; Makrolactonisierungen ; Metathesis ; Naturstoffe ; Olefinmetathesen ; Olefins ; Segments ; Synthesis ; Totalsynthesen ; Veresterungen</subject><ispartof>Angewandte Chemie, 2015-11, Vol.127 (47), p.14380-14384</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright Wiley Subscription Services, Inc. Nov 2015</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3295-f228eaf26d7bfb37ea234ba47d867d42d2bef3e34e664e3fcdb2ca608437bfe3</citedby><cites>FETCH-LOGICAL-c3295-f228eaf26d7bfb37ea234ba47d867d42d2bef3e34e664e3fcdb2ca608437bfe3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fange.201507795$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fange.201507795$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Kita, Masaki</creatorcontrib><creatorcontrib>Oka, Hirotaka</creatorcontrib><creatorcontrib>Usui, Akihiro</creatorcontrib><creatorcontrib>Ishitsuka, Tomoya</creatorcontrib><creatorcontrib>Mogi, Yuzo</creatorcontrib><creatorcontrib>Watanabe, Hidekazu</creatorcontrib><creatorcontrib>Tsunoda, Masaki</creatorcontrib><creatorcontrib>Kigoshi, Hideo</creatorcontrib><title>Total Synthesis of Mycalolides A and B through Olefin Metathesis</title><title>Angewandte Chemie</title><description>An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1–C19 trisoxazole and C20–C35 side‐chain segments through the use of olefin metathesis and esterification as well as Julia–Kocienski olefination and enamide formation as key steps.
Von Anfang an: Eine asymmetrische Totalsynthese der Trisoxazol‐Makrolide Mycalolid A und B beruht auf dem konvergenten Aufbau des Trisoxazolmotivs C1–C19 und des Seitenkettensegments C20–C35 mit Olefinmetathese und Veresterung als Schlüsselschritten.</description><subject>Assembly</subject><subject>Asymmetry</subject><subject>Chemistry</subject><subject>Decomposition reactions</subject><subject>Esterification</subject><subject>Formations</subject><subject>Makrolactonisierungen</subject><subject>Metathesis</subject><subject>Naturstoffe</subject><subject>Olefinmetathesen</subject><subject>Olefins</subject><subject>Segments</subject><subject>Synthesis</subject><subject>Totalsynthesen</subject><subject>Veresterungen</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOwzAQQC0EEqWwMltiYUmxz06cbBRUClJLB7pbTnJuU6VxiROh_D2pgkBigOmW9053j5BrziacMbgz1QYnwHjIlErCEzLiIfBAqFCdkhFjUgYxyOScXHi_Y4xFoJIRuV-7xpT0rauaLfrCU2fpsstM6coiR0-n1FQ5faDNtnbtZktXJdqioktszCBckjNrSo9XX3NM1k-z9eNzsFjNXx6niyATkISBBYjRWIhyldpUKDQgZGqkyuNI5RJySNEKFBKjSKKwWZ5CZiIWS9ELKMbkdlh7qN17i77R-8JnWJamQtd6zeP-w5hxiHr05he6c21d9cdpCCPgksm_Kd4nYyETIHpqMlBZ7byv0epDXexN3WnO9LG6PlbX39V7IRmEj6LE7h9aT1_nsx_3E7muhI4</recordid><startdate>20151116</startdate><enddate>20151116</enddate><creator>Kita, Masaki</creator><creator>Oka, Hirotaka</creator><creator>Usui, Akihiro</creator><creator>Ishitsuka, Tomoya</creator><creator>Mogi, Yuzo</creator><creator>Watanabe, Hidekazu</creator><creator>Tsunoda, Masaki</creator><creator>Kigoshi, Hideo</creator><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20151116</creationdate><title>Total Synthesis of Mycalolides A and B through Olefin Metathesis</title><author>Kita, Masaki ; Oka, Hirotaka ; Usui, Akihiro ; Ishitsuka, Tomoya ; Mogi, Yuzo ; Watanabe, Hidekazu ; Tsunoda, Masaki ; Kigoshi, Hideo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3295-f228eaf26d7bfb37ea234ba47d867d42d2bef3e34e664e3fcdb2ca608437bfe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Assembly</topic><topic>Asymmetry</topic><topic>Chemistry</topic><topic>Decomposition reactions</topic><topic>Esterification</topic><topic>Formations</topic><topic>Makrolactonisierungen</topic><topic>Metathesis</topic><topic>Naturstoffe</topic><topic>Olefinmetathesen</topic><topic>Olefins</topic><topic>Segments</topic><topic>Synthesis</topic><topic>Totalsynthesen</topic><topic>Veresterungen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kita, Masaki</creatorcontrib><creatorcontrib>Oka, Hirotaka</creatorcontrib><creatorcontrib>Usui, Akihiro</creatorcontrib><creatorcontrib>Ishitsuka, Tomoya</creatorcontrib><creatorcontrib>Mogi, Yuzo</creatorcontrib><creatorcontrib>Watanabe, Hidekazu</creatorcontrib><creatorcontrib>Tsunoda, Masaki</creatorcontrib><creatorcontrib>Kigoshi, Hideo</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kita, Masaki</au><au>Oka, Hirotaka</au><au>Usui, Akihiro</au><au>Ishitsuka, Tomoya</au><au>Mogi, Yuzo</au><au>Watanabe, Hidekazu</au><au>Tsunoda, Masaki</au><au>Kigoshi, Hideo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Mycalolides A and B through Olefin Metathesis</atitle><jtitle>Angewandte Chemie</jtitle><date>2015-11-16</date><risdate>2015</risdate><volume>127</volume><issue>47</issue><spage>14380</spage><epage>14384</epage><pages>14380-14384</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>An asymmetric total synthesis of the trisoxazole marine macrolides mycalolides A and B is described. This synthesis involves the convergent assembly of highly functionalized C1–C19 trisoxazole and C20–C35 side‐chain segments through the use of olefin metathesis and esterification as well as Julia–Kocienski olefination and enamide formation as key steps.
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| subjects | Assembly Asymmetry Chemistry Decomposition reactions Esterification Formations Makrolactonisierungen Metathesis Naturstoffe Olefinmetathesen Olefins Segments Synthesis Totalsynthesen Veresterungen |
| title | Total Synthesis of Mycalolides A and B through Olefin Metathesis |
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