Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene
Three keto-carotenoids were prepared by the oxidation of the stable C40 trisulfone 6, which has been used as the key compound in our β-carotene synthesis. The first allylic oxidation to the unsaturated ketone and the second oxidation to the α-hydroxyketone produced the C40 trisulfones 7 and 10, resp...
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| Veröffentlicht in: | Journal of organic chemistry 2005-04, Vol.70 (8), p.3328-3331 |
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| container_title | Journal of organic chemistry |
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| creator | Choi, Seyoung Koo, Sangho |
| description | Three keto-carotenoids were prepared by the oxidation of the stable C40 trisulfone 6, which has been used as the key compound in our β-carotene synthesis. The first allylic oxidation to the unsaturated ketone and the second oxidation to the α-hydroxyketone produced the C40 trisulfones 7 and 10, respectively. The Ramberg−Bäcklund reaction of the oxidized C40 trisulfone was efficiently effected by the use of a mild base, NaOMe, in the presence of CCl4 as a halogenating agent to give the C40 disulfones 8 and 11. Base-promoted dehydrosulfonation reaction of the disulfone compounds produced the fully conjugated polyenes of canthaxanthin (1), astaxanthin (2), and astacene (3). |
| doi_str_mv | 10.1021/jo050101l |
| format | Article |
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The first allylic oxidation to the unsaturated ketone and the second oxidation to the α-hydroxyketone produced the C40 trisulfones 7 and 10, respectively. The Ramberg−Bäcklund reaction of the oxidized C40 trisulfone was efficiently effected by the use of a mild base, NaOMe, in the presence of CCl4 as a halogenating agent to give the C40 disulfones 8 and 11. 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Org. Chem</addtitle><description>Three keto-carotenoids were prepared by the oxidation of the stable C40 trisulfone 6, which has been used as the key compound in our β-carotene synthesis. The first allylic oxidation to the unsaturated ketone and the second oxidation to the α-hydroxyketone produced the C40 trisulfones 7 and 10, respectively. The Ramberg−Bäcklund reaction of the oxidized C40 trisulfone was efficiently effected by the use of a mild base, NaOMe, in the presence of CCl4 as a halogenating agent to give the C40 disulfones 8 and 11. Base-promoted dehydrosulfonation reaction of the disulfone compounds produced the fully conjugated polyenes of canthaxanthin (1), astaxanthin (2), and astacene (3).</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>beta Carotene - analogs & derivatives</subject><subject>beta Carotene - chemical synthesis</subject><subject>Canthaxanthin - chemical synthesis</subject><subject>Carotenoids - chemical synthesis</subject><subject>Chemistry</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Exact sciences and technology</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Preparations and properties</subject><subject>Terpenoids</subject><subject>Xanthophylls</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkF9LwzAUxYMobk4f_ALSFwXBav60afs45nTiQGETfQtpeoPVLp1JB9u3N3NlfTEPN_cmP849HITOCb4lmJK7rxrHmGBSHaA-iSkOeYajQ9THmNKQUc566MS5L-xPHMfHqEfilDKMsz6aj7UuVQmmCWYb03yCAxfUOvBd8AxNHSpp6wZMXRYuGElPyPW2luYmGLqmG6Qp_h4UGDhFR1pWDs7ae4DeHsbz0SScvjw-jYbTULKUNCEvFKQ8onme5RDlRcpIpKjvMmBFknISUUiSQnrTDCToSGuVE41lwbXKOGMDdLXTXdr6ZwWuEYvSKagqaaBeOcGThPEs24LXO1DZ2jkLWixtuZB2IwgW2wjFPkLPXrSiq3wBRUe2mXngsgWkU7LSVhpVuo7jfmWKqefCHVe6Btb7f2m_vTGWxGL-OhOTmN_P3meJ-Oh0pXLez8oan90_Bn8BTjmUvw</recordid><startdate>20050415</startdate><enddate>20050415</enddate><creator>Choi, Seyoung</creator><creator>Koo, Sangho</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050415</creationdate><title>Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene</title><author>Choi, Seyoung ; Koo, Sangho</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-6dce8642bb9be4bd8314c2e4b9e3d786142e77da0553eaef4ffcb1f0ad6fc9633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>beta Carotene - analogs & derivatives</topic><topic>beta Carotene - chemical synthesis</topic><topic>Canthaxanthin - chemical synthesis</topic><topic>Carotenoids - chemical synthesis</topic><topic>Chemistry</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Exact sciences and technology</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Oxidation-Reduction</topic><topic>Preparations and properties</topic><topic>Terpenoids</topic><topic>Xanthophylls</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Choi, Seyoung</creatorcontrib><creatorcontrib>Koo, Sangho</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Choi, Seyoung</au><au>Koo, Sangho</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-04-15</date><risdate>2005</risdate><volume>70</volume><issue>8</issue><spage>3328</spage><epage>3331</epage><pages>3328-3331</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Three keto-carotenoids were prepared by the oxidation of the stable C40 trisulfone 6, which has been used as the key compound in our β-carotene synthesis. The first allylic oxidation to the unsaturated ketone and the second oxidation to the α-hydroxyketone produced the C40 trisulfones 7 and 10, respectively. The Ramberg−Bäcklund reaction of the oxidized C40 trisulfone was efficiently effected by the use of a mild base, NaOMe, in the presence of CCl4 as a halogenating agent to give the C40 disulfones 8 and 11. Base-promoted dehydrosulfonation reaction of the disulfone compounds produced the fully conjugated polyenes of canthaxanthin (1), astaxanthin (2), and astacene (3).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15823009</pmid><doi>10.1021/jo050101l</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2005-04, Vol.70 (8), p.3328-3331 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids beta Carotene - analogs & derivatives beta Carotene - chemical synthesis Canthaxanthin - chemical synthesis Carotenoids - chemical synthesis Chemistry Combinatorial Chemistry Techniques Exact sciences and technology Molecular Structure Organic chemistry Oxidation-Reduction Preparations and properties Terpenoids Xanthophylls |
| title | Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene |
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