Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin
Abstract The total synthesis of biselide A based on our earlier strategy of synthesizing haterumalides is reported. The highlights of this approach are the use of regioselective enzymatic hydrolysis for the installation of a C20 oxygen functional group and an asymmetric aldol reaction for the stereo...
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Veröffentlicht in: | Synthesis (Stuttgart) 2017-07, Vol.49 (13), p.2958-2970 |
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container_title | Synthesis (Stuttgart) |
container_volume | 49 |
creator | Hayakawa, Ichiro Okamura, Masami Suzuki, Kazuaki Shimanuki, Mami Kimura, Kizuku Yamada, Takuya Ohyoshi, Takayuki Kigoshi, Hideo |
description | Abstract
The total synthesis of biselide A based on our earlier strategy of synthesizing haterumalides is reported. The highlights of this approach are the use of regioselective enzymatic hydrolysis for the installation of a C20 oxygen functional group and an asymmetric aldol reaction for the stereoselective introduction of a C3 oxygen functional group. |
doi_str_mv | 10.1055/s-0036-1588169 |
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The total synthesis of biselide A based on our earlier strategy of synthesizing haterumalides is reported. The highlights of this approach are the use of regioselective enzymatic hydrolysis for the installation of a C20 oxygen functional group and an asymmetric aldol reaction for the stereoselective introduction of a C3 oxygen functional group.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0036-1588169</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2017-07, Vol.49 (13), p.2958-2970</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c343t-3262fb24c158cf0f5cc815b5e2b95bbfd2662588b96ec4d42e64d7532a6997fa3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0036-1588169.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0036-1588169$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Hayakawa, Ichiro</creatorcontrib><creatorcontrib>Okamura, Masami</creatorcontrib><creatorcontrib>Suzuki, Kazuaki</creatorcontrib><creatorcontrib>Shimanuki, Mami</creatorcontrib><creatorcontrib>Kimura, Kizuku</creatorcontrib><creatorcontrib>Yamada, Takuya</creatorcontrib><creatorcontrib>Ohyoshi, Takayuki</creatorcontrib><creatorcontrib>Kigoshi, Hideo</creatorcontrib><title>Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
The total synthesis of biselide A based on our earlier strategy of synthesizing haterumalides is reported. The highlights of this approach are the use of regioselective enzymatic hydrolysis for the installation of a C20 oxygen functional group and an asymmetric aldol reaction for the stereoselective introduction of a C3 oxygen functional group.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1kD1PwzAURS0EEqGwMvsH4OKP2InHEJWC1KoDRWKzHMemrtIE2UEi_x6XdmV6w7336egAcE_wnGDOHyPCmAlEeFkSIS9ARnJWIErwxyXIUiRRkZJrcBPjHmNcUCYzsNgOo-7g29SPOxt9hIODTz7azrcWVg-wgvU0DuPw4w1caxOGvyCV1jr43sJN8J--vwVXTnfR3p3vDLw_L7b1C1ptlq91tUKG5WxEjArqGpqbxGgcdtyYkvCGW9pI3jSupULQhN9IYU3e5tSKvC04o1pIWTjNZmB--ptAYgzWqa_gDzpMimB1lKCiOkpQZwlpgE6Dceftwar98B36RPhf_xcOXVx8</recordid><startdate>20170703</startdate><enddate>20170703</enddate><creator>Hayakawa, Ichiro</creator><creator>Okamura, Masami</creator><creator>Suzuki, Kazuaki</creator><creator>Shimanuki, Mami</creator><creator>Kimura, Kizuku</creator><creator>Yamada, Takuya</creator><creator>Ohyoshi, Takayuki</creator><creator>Kigoshi, Hideo</creator><general>Georg Thieme Verlag</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20170703</creationdate><title>Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin</title><author>Hayakawa, Ichiro ; Okamura, Masami ; Suzuki, Kazuaki ; Shimanuki, Mami ; Kimura, Kizuku ; Yamada, Takuya ; Ohyoshi, Takayuki ; Kigoshi, Hideo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c343t-3262fb24c158cf0f5cc815b5e2b95bbfd2662588b96ec4d42e64d7532a6997fa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hayakawa, Ichiro</creatorcontrib><creatorcontrib>Okamura, Masami</creatorcontrib><creatorcontrib>Suzuki, Kazuaki</creatorcontrib><creatorcontrib>Shimanuki, Mami</creatorcontrib><creatorcontrib>Kimura, Kizuku</creatorcontrib><creatorcontrib>Yamada, Takuya</creatorcontrib><creatorcontrib>Ohyoshi, Takayuki</creatorcontrib><creatorcontrib>Kigoshi, Hideo</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hayakawa, Ichiro</au><au>Okamura, Masami</au><au>Suzuki, Kazuaki</au><au>Shimanuki, Mami</au><au>Kimura, Kizuku</au><au>Yamada, Takuya</au><au>Ohyoshi, Takayuki</au><au>Kigoshi, Hideo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2017-07-03</date><risdate>2017</risdate><volume>49</volume><issue>13</issue><spage>2958</spage><epage>2970</epage><pages>2958-2970</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
The total synthesis of biselide A based on our earlier strategy of synthesizing haterumalides is reported. The highlights of this approach are the use of regioselective enzymatic hydrolysis for the installation of a C20 oxygen functional group and an asymmetric aldol reaction for the stereoselective introduction of a C3 oxygen functional group.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0036-1588169</doi><tpages>13</tpages></addata></record> |
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title | Total Synthesis of Biselide A, A Cytotoxic Macrolide of Marine Origin |
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