The absolute configuration of (+)- and (−)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris
Hydrogenation of the triple bond of (+)-1-phenylundec-4-yn-3-ol (obtained from (+)-[η 6 -(3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH 4 -NiCl 2 ·6H 2 O reagent system in MeOH leads to (−)-1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives...
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| Veröffentlicht in: | Russian chemical bulletin 2013-09, Vol.62 (9), p.2032-2036 |
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| container_title | Russian chemical bulletin |
| container_volume | 62 |
| creator | Vlasyuk, A. L. Voblikova, V. A. Gamalevich, G. D. Serebryakov, E. P. |
| description | Hydrogenation of the triple bond of (+)-1-phenylundec-4-yn-3-ol (obtained from (+)-[η
6
-(3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH
4
-NiCl
2
·6H
2
O reagent system in MeOH leads to (−)-1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives (
R
)-(−)-acetoxydodecanoic acid, lactonization of which leads to the known (
R
)-(+)-4-dodecanolide. The starting (+)-1-phenylundec-4-yn-3-ol was thus shown to have the
S
-configuration. |
| doi_str_mv | 10.1007/s11172-013-0294-8 |
| format | Article |
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6
-(3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH
4
-NiCl
2
·6H
2
O reagent system in MeOH leads to (−)-1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives (
R
)-(−)-acetoxydodecanoic acid, lactonization of which leads to the known (
R
)-(+)-4-dodecanolide. The starting (+)-1-phenylundec-4-yn-3-ol was thus shown to have the
S
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6
-(3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH
4
-NiCl
2
·6H
2
O reagent system in MeOH leads to (−)-1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives (
R
)-(−)-acetoxydodecanoic acid, lactonization of which leads to the known (
R
)-(+)-4-dodecanolide. The starting (+)-1-phenylundec-4-yn-3-ol was thus shown to have the
S
-configuration.</description><subject>Bledius</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Full Articles</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><issn>1066-5285</issn><issn>1573-9171</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kU1uFDEQhVsIJELgAOy8nBE4uPrH7l5CBAEpUiQIa8vtLmcceezB1R1pbsA6V8mNOEk8DNmysuX6XtVzvap6C-IMhFAfCABUzQU0XNRDy_tn1Ql0quEDKHhe7kJK3tV997J6RXQrhKj7vj-pHq43yMxIKSwzMpui8zdLNrNPkSXHVu_WnJk4sdWf3_drDny3wbgPS5zQ8pbvI294CnTGfuzjvEHy9Ff1fV2KUyqQiSn4Cd8zU5pvdylinA9IgdmEDiP5O2SENuPTzJzKy4g4B2SfAk5-IbYtHvy4hGCyp9fVC2cC4Zt_52n188vn6_Ov_PLq4tv5x0tumxpmLmtowZXtdLUYJE52aFUnu3aUfTvgqNANzripFb0crBRDwRVYJaSyaLpONKfV6th3l9OvBWnWW08Wi4mIaSENShy22wAUFI6ozYkoo9O77Lcm7zUIfQhIHwPSJSB9CEj3RVMfNVTYeINZ36Ylx_Kj_4geAbIFk5Y</recordid><startdate>20130901</startdate><enddate>20130901</enddate><creator>Vlasyuk, A. L.</creator><creator>Voblikova, V. A.</creator><creator>Gamalevich, G. D.</creator><creator>Serebryakov, E. P.</creator><general>Springer US</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SS</scope></search><sort><creationdate>20130901</creationdate><title>The absolute configuration of (+)- and (−)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris</title><author>Vlasyuk, A. L. ; Voblikova, V. A. ; Gamalevich, G. D. ; Serebryakov, E. P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c321t-62141f10052096edc9475654b6849eb7ef9fafd40869c60921471c7067cea5503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Bledius</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Full Articles</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vlasyuk, A. L.</creatorcontrib><creatorcontrib>Voblikova, V. A.</creatorcontrib><creatorcontrib>Gamalevich, G. D.</creatorcontrib><creatorcontrib>Serebryakov, E. P.</creatorcontrib><collection>CrossRef</collection><collection>Entomology Abstracts (Full archive)</collection><jtitle>Russian chemical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vlasyuk, A. L.</au><au>Voblikova, V. A.</au><au>Gamalevich, G. D.</au><au>Serebryakov, E. P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The absolute configuration of (+)- and (−)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris</atitle><jtitle>Russian chemical bulletin</jtitle><stitle>Russ Chem Bull</stitle><date>2013-09-01</date><risdate>2013</risdate><volume>62</volume><issue>9</issue><spage>2032</spage><epage>2036</epage><pages>2032-2036</pages><issn>1066-5285</issn><eissn>1573-9171</eissn><abstract>Hydrogenation of the triple bond of (+)-1-phenylundec-4-yn-3-ol (obtained from (+)-[η
6
-(3-hydroxyundec-4-yn-1-yl)benzene]chromium tricarbonyl) with the NaBH
4
-NiCl
2
·6H
2
O reagent system in MeOH leads to (−)-1-phenylundecan-3-ol. Ozonolysis of the phenyl ring in the corresponding acetate gives (
R
)-(−)-acetoxydodecanoic acid, lactonization of which leads to the known (
R
)-(+)-4-dodecanolide. The starting (+)-1-phenylundec-4-yn-3-ol was thus shown to have the
S
-configuration.</abstract><cop>Boston</cop><pub>Springer US</pub><doi>10.1007/s11172-013-0294-8</doi><tpages>5</tpages></addata></record> |
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| language | eng |
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| source | SpringerLink Journals - AutoHoldings |
| subjects | Bledius Chemistry Chemistry and Materials Science Chemistry/Food Science Full Articles Inorganic Chemistry Organic Chemistry |
| title | The absolute configuration of (+)- and (−)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris |
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