Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization
The first total synthesis of (±)-lantalucratins A and B is described. Introduction of an alkyl side chain at the 6-position was proceeded by directed ortho-lithiation and subsequent alkylation reaction to afford 6-alkyl-5,7,8-trimethoxy-1-naphthol as a synthetically important intermediate for (±)-la...
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| Veröffentlicht in: | Tetrahedron 2013-12, Vol.69 (48), p.10470-10476 |
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| container_issue | 48 |
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| container_title | Tetrahedron |
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| creator | Ogata, Tokutaro Sugiyama, Yoshiko Ito, Saki Nakano, Kazuha Torii, Eri Nishiuchi, Arisa Kimachi, Tetsutaro |
| description | The first total synthesis of (±)-lantalucratins A and B is described. Introduction of an alkyl side chain at the 6-position was proceeded by directed ortho-lithiation and subsequent alkylation reaction to afford 6-alkyl-5,7,8-trimethoxy-1-naphthol as a synthetically important intermediate for (±)-lantalucratins A and B in excellent yield with complete regioselectivity. The 1,2-naphthoquinone fused five-membered cyclic ether framework was constructed directly from 3-hydroxyalkyl-naphthalenes by oxidative intramolecular cyclization reaction with diammonium cerium(IV) nitrate. (±)-Lantalucratins A and B were obtained in 69% and 45% overall yields, respectively.
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| doi_str_mv | 10.1016/j.tet.2013.09.081 |
| format | Article |
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[Display omitted]</description><subject>Alkylation</subject><subject>Chain reactions</subject><subject>Chains</subject><subject>Construction</subject><subject>Diammonium cerium(IV) nitrate</subject><subject>Directed ortho-lithiation</subject><subject>Ethers</subject><subject>Naphthoquinone</subject><subject>Natural product</subject><subject>Nitrates</subject><subject>Oxidative cyclization</subject><subject>Synthesis</subject><subject>Tetrahedrons</subject><subject>Total synthesis</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kMFO4zAQhi3ESpTuPsDefCyHhJk4sRNxKhULSBV7KWfLsSfCVZpA7CK6b8Ur7JNhVM6cZjTz_6P5P8Z-I-QIKC-3eaSYF4AihyaHGk_YDEtZZlWJ8pTNAErISijgjJ2HsAUAxELM2GYzRtPzcBjiEwUf-Njxxf_3i6w3Q1rs7WSiHwJfcjM4fs3bA18tH7IdOW8iOT6-eZcUr8Ttwfb-X-rH4Sf70Zk-0K-vOmePf242q7ts_ff2frVcZ1Y0MmYKjHGyk0VrpULXINTCqUYRpBG1pNrSVFWFqpVO1FWlRIeqRmFU0SlHlZizxfHu8zS-7ClEvfPBUp9-p3EfNKqylA3UhUhSPErtNIYwUaefJ78z00Ej6E-CeqsTQf1JUEOjE8HkuTp6KGV49TTpYD0NNmWfyEbtRv-N-wNIoXjV</recordid><startdate>20131202</startdate><enddate>20131202</enddate><creator>Ogata, Tokutaro</creator><creator>Sugiyama, Yoshiko</creator><creator>Ito, Saki</creator><creator>Nakano, Kazuha</creator><creator>Torii, Eri</creator><creator>Nishiuchi, Arisa</creator><creator>Kimachi, Tetsutaro</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20131202</creationdate><title>Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization</title><author>Ogata, Tokutaro ; Sugiyama, Yoshiko ; Ito, Saki ; Nakano, Kazuha ; Torii, Eri ; Nishiuchi, Arisa ; Kimachi, Tetsutaro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c396t-70aad6f62bc671d91083d797e062bebe7b4a55517b6d385573f17813a72f7de53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkylation</topic><topic>Chain reactions</topic><topic>Chains</topic><topic>Construction</topic><topic>Diammonium cerium(IV) nitrate</topic><topic>Directed ortho-lithiation</topic><topic>Ethers</topic><topic>Naphthoquinone</topic><topic>Natural product</topic><topic>Nitrates</topic><topic>Oxidative cyclization</topic><topic>Synthesis</topic><topic>Tetrahedrons</topic><topic>Total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ogata, Tokutaro</creatorcontrib><creatorcontrib>Sugiyama, Yoshiko</creatorcontrib><creatorcontrib>Ito, Saki</creatorcontrib><creatorcontrib>Nakano, Kazuha</creatorcontrib><creatorcontrib>Torii, Eri</creatorcontrib><creatorcontrib>Nishiuchi, Arisa</creatorcontrib><creatorcontrib>Kimachi, Tetsutaro</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ogata, Tokutaro</au><au>Sugiyama, Yoshiko</au><au>Ito, Saki</au><au>Nakano, Kazuha</au><au>Torii, Eri</au><au>Nishiuchi, Arisa</au><au>Kimachi, Tetsutaro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization</atitle><jtitle>Tetrahedron</jtitle><date>2013-12-02</date><risdate>2013</risdate><volume>69</volume><issue>48</issue><spage>10470</spage><epage>10476</epage><pages>10470-10476</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>The first total synthesis of (±)-lantalucratins A and B is described. Introduction of an alkyl side chain at the 6-position was proceeded by directed ortho-lithiation and subsequent alkylation reaction to afford 6-alkyl-5,7,8-trimethoxy-1-naphthol as a synthetically important intermediate for (±)-lantalucratins A and B in excellent yield with complete regioselectivity. The 1,2-naphthoquinone fused five-membered cyclic ether framework was constructed directly from 3-hydroxyalkyl-naphthalenes by oxidative intramolecular cyclization reaction with diammonium cerium(IV) nitrate. (±)-Lantalucratins A and B were obtained in 69% and 45% overall yields, respectively.
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| ispartof | Tetrahedron, 2013-12, Vol.69 (48), p.10470-10476 |
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| language | eng |
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| subjects | Alkylation Chain reactions Chains Construction Diammonium cerium(IV) nitrate Directed ortho-lithiation Ethers Naphthoquinone Natural product Nitrates Oxidative cyclization Synthesis Tetrahedrons Total synthesis |
| title | Total synthesis of (±)-lantalucratins A and B by CAN-mediated oxidative cyclization |
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