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Studies of the synthesis of 8a-hydroxy-4a-methyloctahydronaphthalen-1(2H)-ones and their 2α-deutero derivatives
Two syntheses of the bicyclic α-ketols, 8a-hydroxy-4a-methyl-trans- and -cis-octahydronaphthalen-1(2H)-ones ( 1 and 2 ), have been effected. One involves epoxidation of 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene ( 4 ), followed by hydrolysis and oxidation; direct "hydroxy ketonization"...
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| Published in: | Canadian journal of chemistry 1988-01, Vol.66 (1), p.27-34 |
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| Main Authors: | , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c250t-5f934aa187e55af972e81f9ae3d0c6030a36c02d7fc34ddea9fa53ef758e29dc3 |
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| container_end_page | 34 |
| container_issue | 1 |
| container_start_page | 27 |
| container_title | Canadian journal of chemistry |
| container_volume | 66 |
| creator | Stiver, Shirley Clark, Peter D Yates, Peter |
| description | Two syntheses of the bicyclic α-ketols, 8a-hydroxy-4a-methyl-trans- and -cis-octahydronaphthalen-1(2H)-ones (
1
and
2
), have been effected. One involves epoxidation of 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (
4
), followed by hydrolysis and oxidation; direct "hydroxy ketonization" of
4
was found not to be practicable. The second involves treatment of 3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one (
14
) with lithium dimethylcuprate, trimethylsilylation of the resulting enolate, oxidation of the enol ether, and hydrolysis. Syntheses of the 2α-deutero derivatives of
1
and
2
are also described. |
| doi_str_mv | 10.1139/v88-004 |
| format | article |
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1
and
2
), have been effected. One involves epoxidation of 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (
4
), followed by hydrolysis and oxidation; direct "hydroxy ketonization" of
4
was found not to be practicable. The second involves treatment of 3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one (
14
) with lithium dimethylcuprate, trimethylsilylation of the resulting enolate, oxidation of the enol ether, and hydrolysis. Syntheses of the 2α-deutero derivatives of
1
and
2
are also described.</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v88-004</identifier><identifier>CODEN: CJCHAG</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><subject>Alicyclic compounds ; Alicyclic compounds, terpenoids, prostaglandins, steroids ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Preparations and properties</subject><ispartof>Canadian journal of chemistry, 1988-01, Vol.66 (1), p.27-34</ispartof><rights>1989 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c250t-5f934aa187e55af972e81f9ae3d0c6030a36c02d7fc34ddea9fa53ef758e29dc3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4021,27921,27922,27923</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=7109724$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Stiver, Shirley</creatorcontrib><creatorcontrib>Clark, Peter D</creatorcontrib><creatorcontrib>Yates, Peter</creatorcontrib><title>Studies of the synthesis of 8a-hydroxy-4a-methyloctahydronaphthalen-1(2H)-ones and their 2α-deutero derivatives</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>Two syntheses of the bicyclic α-ketols, 8a-hydroxy-4a-methyl-trans- and -cis-octahydronaphthalen-1(2H)-ones (
1
and
2
), have been effected. One involves epoxidation of 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (
4
), followed by hydrolysis and oxidation; direct "hydroxy ketonization" of
4
was found not to be practicable. The second involves treatment of 3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one (
14
) with lithium dimethylcuprate, trimethylsilylation of the resulting enolate, oxidation of the enol ether, and hydrolysis. Syntheses of the 2α-deutero derivatives of
1
and
2
are also described.</description><subject>Alicyclic compounds</subject><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><recordid>eNp1kMtKxDAUhoMoOI7iK3Qh3iCaSztNlzKoIwy4UNflkJzQSqctSWawj-WL-ExmLsxCcPVzDh_fDz8h55zdcS6L-5VSlLH0gIx4qhiVouCHZMQYUzRlqTgmJ95_xjNnIhuR_i0sTY0-6WwSKkz80Mbw9eahgFaDcd3XQFOgCwzV0HQ6wObZQl-FChpsKb8WsxvatVEDrVl7apeIn29qcBnQdYlBV68g1Cv0p-TIQuPxbJdj8vH0-D6d0fnr88v0YU61yFigmS1kCsBVjlkGtsgFKm4LQGmYnjDJQE40Eya3WqbGIBQWMok2zxSKwmg5Jldbr3ad9w5t2bt6AW4oOSvXQ5VxqDIOFcmLLdmD19BYB62u_R7POYvta-xyi7VOO_QITld7aOcqe2MjePs_-Lf8F10MhdI</recordid><startdate>19880101</startdate><enddate>19880101</enddate><creator>Stiver, Shirley</creator><creator>Clark, Peter D</creator><creator>Yates, Peter</creator><general>NRC Research Press</general><general>National Research Council of Canada</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19880101</creationdate><title>Studies of the synthesis of 8a-hydroxy-4a-methyloctahydronaphthalen-1(2H)-ones and their 2α-deutero derivatives</title><author>Stiver, Shirley ; Clark, Peter D ; Yates, Peter</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c250t-5f934aa187e55af972e81f9ae3d0c6030a36c02d7fc34ddea9fa53ef758e29dc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>Alicyclic compounds</topic><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Stiver, Shirley</creatorcontrib><creatorcontrib>Clark, Peter D</creatorcontrib><creatorcontrib>Yates, Peter</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Stiver, Shirley</au><au>Clark, Peter D</au><au>Yates, Peter</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies of the synthesis of 8a-hydroxy-4a-methyloctahydronaphthalen-1(2H)-ones and their 2α-deutero derivatives</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1988-01-01</date><risdate>1988</risdate><volume>66</volume><issue>1</issue><spage>27</spage><epage>34</epage><pages>27-34</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><coden>CJCHAG</coden><abstract>Two syntheses of the bicyclic α-ketols, 8a-hydroxy-4a-methyl-trans- and -cis-octahydronaphthalen-1(2H)-ones (
1
and
2
), have been effected. One involves epoxidation of 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (
4
), followed by hydrolysis and oxidation; direct "hydroxy ketonization" of
4
was found not to be practicable. The second involves treatment of 3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one (
14
) with lithium dimethylcuprate, trimethylsilylation of the resulting enolate, oxidation of the enol ether, and hydrolysis. Syntheses of the 2α-deutero derivatives of
1
and
2
are also described.</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v88-004</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-4042 |
| ispartof | Canadian journal of chemistry, 1988-01, Vol.66 (1), p.27-34 |
| issn | 0008-4042 1480-3291 |
| language | eng |
| recordid | cdi_pascalfrancis_primary_7109724 |
| source | EZB-FREE-00999 freely available EZB journals |
| subjects | Alicyclic compounds Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Organic chemistry Preparations and properties |
| title | Studies of the synthesis of 8a-hydroxy-4a-methyloctahydronaphthalen-1(2H)-ones and their 2α-deutero derivatives |
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