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General Approach to 2,3-Dibenzyl-γ-butyrolactone Lignans: Application to the Total Synthesis of (±)-5′-Methoxyyatein, (±)-5′-Methoxyclusin, and (±)-4′-Hydroxycubebinone
The total synthesis of natural lignans 5′‐methoxyyatein (1), 5′‐methoxyclusin (2), and 4′‐hydroxycubebinone (3), in racemic form, has been achieved by a newly developed strategy, wherein lithium naphthalenide induced decyanation was employed as a key operation to establish the essential trans config...
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| Published in: | European Journal of Organic Chemistry 2010-06, Vol.2010 (18), p.3473-3480 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c3578-d0609570497d8aaac8994f84d00f344f4a93bb5084676f4291c3e6495224b5103 |
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| cites | cdi_FETCH-LOGICAL-c3578-d0609570497d8aaac8994f84d00f344f4a93bb5084676f4291c3e6495224b5103 |
| container_end_page | 3480 |
| container_issue | 18 |
| container_start_page | 3473 |
| container_title | European Journal of Organic Chemistry |
| container_volume | 2010 |
| creator | Amancha, Prashanth K. Liu, Hsing-Jang Ly, Tai Wei Shia, Kak-Shan |
| description | The total synthesis of natural lignans 5′‐methoxyyatein (1), 5′‐methoxyclusin (2), and 4′‐hydroxycubebinone (3), in racemic form, has been achieved by a newly developed strategy, wherein lithium naphthalenide induced decyanation was employed as a key operation to establish the essential trans configuration of the butyrolactone ring.
A concise synthetic route to the 2,3‐dibenzylbutyrolactone core has been developed, whereby the total synthesis of natural lignans 1, 2, and 3, in racemic form, in an overall yield of 25, 18, and 19 %, respectively, has been accomplished. |
| doi_str_mv | 10.1002/ejoc.201000318 |
| format | article |
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A concise synthetic route to the 2,3‐dibenzylbutyrolactone core has been developed, whereby the total synthesis of natural lignans 1, 2, and 3, in racemic form, in an overall yield of 25, 18, and 19 %, respectively, has been accomplished.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201000318</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Lactones ; Lignans ; Natural products ; Organic chemistry ; Preparations and properties ; Synthetic methods ; Total synthesis</subject><ispartof>European Journal of Organic Chemistry, 2010-06, Vol.2010 (18), p.3473-3480</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3578-d0609570497d8aaac8994f84d00f344f4a93bb5084676f4291c3e6495224b5103</citedby><cites>FETCH-LOGICAL-c3578-d0609570497d8aaac8994f84d00f344f4a93bb5084676f4291c3e6495224b5103</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>313,314,780,784,792,27922,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22922890$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Amancha, Prashanth K.</creatorcontrib><creatorcontrib>Liu, Hsing-Jang</creatorcontrib><creatorcontrib>Ly, Tai Wei</creatorcontrib><creatorcontrib>Shia, Kak-Shan</creatorcontrib><title>General Approach to 2,3-Dibenzyl-γ-butyrolactone Lignans: Application to the Total Synthesis of (±)-5′-Methoxyyatein, (±)-5′-Methoxyclusin, and (±)-4′-Hydroxycubebinone</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The total synthesis of natural lignans 5′‐methoxyyatein (1), 5′‐methoxyclusin (2), and 4′‐hydroxycubebinone (3), in racemic form, has been achieved by a newly developed strategy, wherein lithium naphthalenide induced decyanation was employed as a key operation to establish the essential trans configuration of the butyrolactone ring.
A concise synthetic route to the 2,3‐dibenzylbutyrolactone core has been developed, whereby the total synthesis of natural lignans 1, 2, and 3, in racemic form, in an overall yield of 25, 18, and 19 %, respectively, has been accomplished.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Lactones</subject><subject>Lignans</subject><subject>Natural products</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Synthetic methods</subject><subject>Total synthesis</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkMtO3DAUhiNUJCjttutskKiEp77l4u7QQIdWA0gdKthZJ47DmKb2yPaopKu-Uukb8AA8BE9ColSjSl105WN95_tt_UnyhuAJwZi-07dOTSjuZ8xIuZXsEiwEwrnAL_qZM46IYNc7ycsQbvsdkedkN7mfaas9tOnRauUdqGUaXUoPGTo2lbY_uhY9_kbVOnbetaCiszqdmxsLNrwflNYoiMbZwYpLnV662GctOttfggmpa9KDh19vUfb08x6d6bh0d10HURt7-C9Q7ToMAGw9Qj7A0672A1xXujK2_8CrZLuBNujXf8695MuHk8vpKZpfzD5Oj-ZIsawoUY1zLLICc1HUJQCoUgjelLzGuGGcNxwEq6oMlzwv8oZTQRTTORcZpbzKCGZ7yWTMVd6F4HUjV958A99JguXQuBwal5vGe2F_FFYQFLSNB6tM2FiUCkpLMQSLce-7aXX3n1R58uli-vcbaHRNiPpu44L_KvOCFZm8Op_Jq6JcnHP2WS7YM08TpyA</recordid><startdate>201006</startdate><enddate>201006</enddate><creator>Amancha, Prashanth K.</creator><creator>Liu, Hsing-Jang</creator><creator>Ly, Tai Wei</creator><creator>Shia, Kak-Shan</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201006</creationdate><title>General Approach to 2,3-Dibenzyl-γ-butyrolactone Lignans: Application to the Total Synthesis of (±)-5′-Methoxyyatein, (±)-5′-Methoxyclusin, and (±)-4′-Hydroxycubebinone</title><author>Amancha, Prashanth K. ; Liu, Hsing-Jang ; Ly, Tai Wei ; Shia, Kak-Shan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3578-d0609570497d8aaac8994f84d00f344f4a93bb5084676f4291c3e6495224b5103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Lactones</topic><topic>Lignans</topic><topic>Natural products</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Synthetic methods</topic><topic>Total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Amancha, Prashanth K.</creatorcontrib><creatorcontrib>Liu, Hsing-Jang</creatorcontrib><creatorcontrib>Ly, Tai Wei</creatorcontrib><creatorcontrib>Shia, Kak-Shan</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Amancha, Prashanth K.</au><au>Liu, Hsing-Jang</au><au>Ly, Tai Wei</au><au>Shia, Kak-Shan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>General Approach to 2,3-Dibenzyl-γ-butyrolactone Lignans: Application to the Total Synthesis of (±)-5′-Methoxyyatein, (±)-5′-Methoxyclusin, and (±)-4′-Hydroxycubebinone</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2010-06</date><risdate>2010</risdate><volume>2010</volume><issue>18</issue><spage>3473</spage><epage>3480</epage><pages>3473-3480</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The total synthesis of natural lignans 5′‐methoxyyatein (1), 5′‐methoxyclusin (2), and 4′‐hydroxycubebinone (3), in racemic form, has been achieved by a newly developed strategy, wherein lithium naphthalenide induced decyanation was employed as a key operation to establish the essential trans configuration of the butyrolactone ring.
A concise synthetic route to the 2,3‐dibenzylbutyrolactone core has been developed, whereby the total synthesis of natural lignans 1, 2, and 3, in racemic form, in an overall yield of 25, 18, and 19 %, respectively, has been accomplished.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201000318</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1434-193X |
| ispartof | European Journal of Organic Chemistry, 2010-06, Vol.2010 (18), p.3473-3480 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ejoc_201000318 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Lactones Lignans Natural products Organic chemistry Preparations and properties Synthetic methods Total synthesis |
| title | General Approach to 2,3-Dibenzyl-γ-butyrolactone Lignans: Application to the Total Synthesis of (±)-5′-Methoxyyatein, (±)-5′-Methoxyclusin, and (±)-4′-Hydroxycubebinone |
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