Novel and Efficient Syntheses of Four Useful Shikimate- derived Epoxy Chiral Building Blocks via Cyclic Sulfite Intermediates
All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-l-ene-carboxylate （la--ld） are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant （--）-shikimic acid （2） via cyclic sulfite intermediates are described...
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| Veröffentlicht in: | Chinese journal of chemistry 2012-12, Vol.30 (12), p.2759-2766 |
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| container_title | Chinese journal of chemistry |
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| creator | Quan, Na Nie, Liangdeng Shi, Xiaoxin Zhu, Ruiheng Lü, Xia |
| description | All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-l-ene-carboxylate （la--ld） are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant （--）-shikimic acid （2） via cyclic sulfite intermediates are described in this article. The targeted compound （3R,4R,5S）-la was synthesized via four steps from （--）-shikimic acid in 79% overall yield. The other three targeted compounds （3S,4R,5S）-lb, （3S,4S,5R）-1c and （3R,4S,5R）-ld were synthesized via seven steps from （--）-shikimic acid in 56%, 64% and 65% overall yields, respectively. |
| doi_str_mv | 10.1002/cjoc.201201000 |
| format | Article |
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Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant （--）-shikimic acid （2） via cyclic sulfite intermediates are described in this article. The targeted compound （3R,4R,5S）-la was synthesized via four steps from （--）-shikimic acid in 79% overall yield. The other three targeted compounds （3S,4R,5S）-lb, （3S,4S,5R）-1c and （3R,4S,5R）-ld were synthesized via seven steps from （--）-shikimic acid in 56%, 64% and 65% overall yields, respectively.</description><subject>chiron</subject><subject>cyclic sulfite</subject><subject>epoxide</subject><subject>shikimic acid</subject><subject>synthesis</subject><subject>亚硫酸盐</subject><subject>合成中间体</subject><subject>循环</subject><subject>手性</subject><subject>环氧</subject><subject>砌块</subject><subject>莽草酸</subject><subject>衍生</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkM1v0zAYhyMEEmNw5WzEOeV1bMfJkUb7QlMn0Y1xszzn9erWSzo76ZYD_zueOlXckCy9PjzP-_HLss8UZhSg-GbWvZkVQNMDgDfZES0pzyWU4m36A9C8BP77ffYhxnXipSzKo-zPot-hJ7pryYm1zjjsBrKcumGFESPpLTntx0BuItrRk-XKbdyDHjAnLQa3w2Rt--eJNCsXtCfz0fnWdfdk7nuziWTnNGkm450hy9FbNyC56AYMD9i61CV-zN5Z7SN-eq3H2c3pyXVznl9enV003y9zwyoKuaxbxipALkBKhkhRC1NxMNbYOyG1FIbVQtctbau2siXUor0zvMRK67JCzo6zr_u-29A_jhgHtU5XdWmkogVndcVrKBM121Mm9DEGtGob0rVhUhTUS8TqJWJ1iDgJ9V54ch6n_9Cq-XHV_Ovme9fFAZ8Prg4bVUomhbpdnKnzxe0vcT3_qVjiv7wut-q7-8cU8sHhXAIvCsH-Atndm20</recordid><startdate>201212</startdate><enddate>201212</enddate><creator>Quan, Na</creator><creator>Nie, Liangdeng</creator><creator>Shi, Xiaoxin</creator><creator>Zhu, Ruiheng</creator><creator>Lü, Xia</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>2RA</scope><scope>92L</scope><scope>CQIGP</scope><scope>~WA</scope><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201212</creationdate><title>Novel and Efficient Syntheses of Four Useful Shikimate- derived Epoxy Chiral Building Blocks via Cyclic Sulfite Intermediates</title><author>Quan, Na ; Nie, Liangdeng ; Shi, Xiaoxin ; Zhu, Ruiheng ; Lü, Xia</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3810-79d3380e450773ee1ea5c840cfcfb57a75c395a9d1d8d8f6095dbc46e8aa68e43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>chiron</topic><topic>cyclic sulfite</topic><topic>epoxide</topic><topic>shikimic acid</topic><topic>synthesis</topic><topic>亚硫酸盐</topic><topic>合成中间体</topic><topic>循环</topic><topic>手性</topic><topic>环氧</topic><topic>砌块</topic><topic>莽草酸</topic><topic>衍生</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Quan, Na</creatorcontrib><creatorcontrib>Nie, Liangdeng</creatorcontrib><creatorcontrib>Shi, Xiaoxin</creatorcontrib><creatorcontrib>Zhu, Ruiheng</creatorcontrib><creatorcontrib>Lü, Xia</creatorcontrib><collection>中文科技期刊数据库</collection><collection>中文科技期刊数据库-CALIS站点</collection><collection>中文科技期刊数据库-7.0平台</collection><collection>中文科技期刊数据库- 镜像站点</collection><collection>Istex</collection><collection>CrossRef</collection><jtitle>Chinese journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Quan, Na</au><au>Nie, Liangdeng</au><au>Shi, Xiaoxin</au><au>Zhu, Ruiheng</au><au>Lü, Xia</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel and Efficient Syntheses of Four Useful Shikimate- derived Epoxy Chiral Building Blocks via Cyclic Sulfite Intermediates</atitle><jtitle>Chinese journal of chemistry</jtitle><addtitle>Chinese Journal of Chemistry</addtitle><date>2012-12</date><risdate>2012</risdate><volume>30</volume><issue>12</issue><spage>2759</spage><epage>2766</epage><pages>2759-2766</pages><issn>1001-604X</issn><eissn>1614-7065</eissn><abstract>All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-l-ene-carboxylate （la--ld） are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abun- dant （--）-shikimic acid （2） via cyclic sulfite intermediates are described in this article. The targeted compound （3R,4R,5S）-la was synthesized via four steps from （--）-shikimic acid in 79% overall yield. The other three targeted compounds （3S,4R,5S）-lb, （3S,4S,5R）-1c and （3R,4S,5R）-ld were synthesized via seven steps from （--）-shikimic acid in 56%, 64% and 65% overall yields, respectively.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/cjoc.201201000</doi><tpages>8</tpages></addata></record> |
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| subjects | chiron cyclic sulfite epoxide shikimic acid synthesis 亚硫酸盐 合成中间体 循环 手性 环氧 砌块 莽草酸 衍生 |
| title | Novel and Efficient Syntheses of Four Useful Shikimate- derived Epoxy Chiral Building Blocks via Cyclic Sulfite Intermediates |
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