A new approach to 19-nor-A-ring phosphine oxide for the convergent synthesis of 19-nor-calcitriol
•An efficient synthesis of 19-nor-A-ring phospine oxide (5) was achieved from (S)-carvone (7%, 15 steps).•A convergent synthesis of 1α,25-dihydroxy-19-norvitamin D3 (3) was achieved from (S)-carvone and Inhoffen-Lythgoe diol (20 steps, 3%).•The triene system assembly is based on a Wittig-Horner coup...
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| Veröffentlicht in: | The Journal of steroid biochemistry and molecular biology 2017-10, Vol.173, p.86-88 |
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| container_title | The Journal of steroid biochemistry and molecular biology |
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| creator | Sigüeiro, Rita Otero, Rocio González-Berdullas, Patricia Loureiro, Julian Mouriño, Antonio Maestro, Miguel A. |
| description | •An efficient synthesis of 19-nor-A-ring phospine oxide (5) was achieved from (S)-carvone (7%, 15 steps).•A convergent synthesis of 1α,25-dihydroxy-19-norvitamin D3 (3) was achieved from (S)-carvone and Inhoffen-Lythgoe diol (20 steps, 3%).•The triene system assembly is based on a Wittig-Horner coupling.
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A new approach to 19-nor-A-ring phosphine oxide 5 together with a convergent synthesis of the vitamin D3 analogue 1α,25-dihydroxy-19-norvitamin D3 (3) have been developed. The 19-nor-A-ring is constructed from (S)-carvone. The triene system is assembled by a Wittig-Horner coupling. |
| doi_str_mv | 10.1016/j.jsbmb.2016.08.008 |
| format | Article |
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A new approach to 19-nor-A-ring phosphine oxide 5 together with a convergent synthesis of the vitamin D3 analogue 1α,25-dihydroxy-19-norvitamin D3 (3) have been developed. The 19-nor-A-ring is constructed from (S)-carvone. The triene system is assembled by a Wittig-Horner coupling.</description><identifier>ISSN: 0960-0760</identifier><identifier>EISSN: 1879-1220</identifier><identifier>DOI: 10.1016/j.jsbmb.2016.08.008</identifier><identifier>PMID: 27592138</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>19-Nor-A-ring phosphine oxide ; 19-Nor-calcitriol ; Calcitriol - analogs & derivatives ; Calcitriol - chemical synthesis ; Chemistry Techniques, Synthetic - methods ; Convergent synthesis ; Monoterpenes - chemical synthesis ; Monoterpenes - chemistry ; Oxides - chemical synthesis ; Oxides - chemistry ; Phosphines - chemical synthesis ; Phosphines - chemistry ; Vitamin D3 metabolites ; Vitamins - chemical synthesis ; Vitamins - chemistry</subject><ispartof>The Journal of steroid biochemistry and molecular biology, 2017-10, Vol.173, p.86-88</ispartof><rights>2016 Elsevier Ltd</rights><rights>Copyright © 2016 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c425t-7e2cc95632bb5f8006ecd25d34a3555339f320ffd7ee6e4be5701570cf2ede7b3</citedby><cites>FETCH-LOGICAL-c425t-7e2cc95632bb5f8006ecd25d34a3555339f320ffd7ee6e4be5701570cf2ede7b3</cites><orcidid>0000-0001-8922-8033</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.jsbmb.2016.08.008$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27907,27908,45978</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27592138$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sigüeiro, Rita</creatorcontrib><creatorcontrib>Otero, Rocio</creatorcontrib><creatorcontrib>González-Berdullas, Patricia</creatorcontrib><creatorcontrib>Loureiro, Julian</creatorcontrib><creatorcontrib>Mouriño, Antonio</creatorcontrib><creatorcontrib>Maestro, Miguel A.</creatorcontrib><title>A new approach to 19-nor-A-ring phosphine oxide for the convergent synthesis of 19-nor-calcitriol</title><title>The Journal of steroid biochemistry and molecular biology</title><addtitle>J Steroid Biochem Mol Biol</addtitle><description>•An efficient synthesis of 19-nor-A-ring phospine oxide (5) was achieved from (S)-carvone (7%, 15 steps).•A convergent synthesis of 1α,25-dihydroxy-19-norvitamin D3 (3) was achieved from (S)-carvone and Inhoffen-Lythgoe diol (20 steps, 3%).•The triene system assembly is based on a Wittig-Horner coupling.
[Display omitted]
A new approach to 19-nor-A-ring phosphine oxide 5 together with a convergent synthesis of the vitamin D3 analogue 1α,25-dihydroxy-19-norvitamin D3 (3) have been developed. The 19-nor-A-ring is constructed from (S)-carvone. The triene system is assembled by a Wittig-Horner coupling.</description><subject>19-Nor-A-ring phosphine oxide</subject><subject>19-Nor-calcitriol</subject><subject>Calcitriol - analogs & derivatives</subject><subject>Calcitriol - chemical synthesis</subject><subject>Chemistry Techniques, Synthetic - methods</subject><subject>Convergent synthesis</subject><subject>Monoterpenes - chemical synthesis</subject><subject>Monoterpenes - chemistry</subject><subject>Oxides - chemical synthesis</subject><subject>Oxides - chemistry</subject><subject>Phosphines - chemical synthesis</subject><subject>Phosphines - chemistry</subject><subject>Vitamin D3 metabolites</subject><subject>Vitamins - chemical synthesis</subject><subject>Vitamins - chemistry</subject><issn>0960-0760</issn><issn>1879-1220</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEFP3DAQha2KqmwpvwAJ-cglYWyv4_jAYYUoVELi0p6txBmzXmXtYGeh_PsaduHYw2g0o_fmaT5CzhjUDFhzuak3ud_2NS9DDW0N0H4hC9YqXTHO4YgsQDdQgWrgmHzPeQMAQjD1jRxzJTVnol2QbkUDvtBumlLs7JrOkTJdhZiqVZV8eKTTOuZp7QPS-NcPSF1MdF4jtTE8Y3rEMNP8Gsom-0yj-3DbbrR-Tj6OP8hX140ZTw_9hPz5efP7-q66f7j9db26r-ySy7lSyK3VshG876VrARq0A5eDWHZCSimEdoKDc4NCbHDZo1TASlnHcUDVixNysb9bPnnaYZ7N1meL49gFjLtsWCu14kJrXaRiL7Up5pzQmSn5bZdeDQPzxtZszDtb88bWQGsK2-I6PwTs-i0On54PmEVwtRdgefPZYzLZegwWB5_QzmaI_r8B_wCAhYuE</recordid><startdate>201710</startdate><enddate>201710</enddate><creator>Sigüeiro, Rita</creator><creator>Otero, Rocio</creator><creator>González-Berdullas, Patricia</creator><creator>Loureiro, Julian</creator><creator>Mouriño, Antonio</creator><creator>Maestro, Miguel A.</creator><general>Elsevier Ltd</general><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><orcidid>https://orcid.org/0000-0001-8922-8033</orcidid></search><sort><creationdate>201710</creationdate><title>A new approach to 19-nor-A-ring phosphine oxide for the convergent synthesis of 19-nor-calcitriol</title><author>Sigüeiro, Rita ; Otero, Rocio ; González-Berdullas, Patricia ; Loureiro, Julian ; Mouriño, Antonio ; Maestro, Miguel A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c425t-7e2cc95632bb5f8006ecd25d34a3555339f320ffd7ee6e4be5701570cf2ede7b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>19-Nor-A-ring phosphine oxide</topic><topic>19-Nor-calcitriol</topic><topic>Calcitriol - analogs & derivatives</topic><topic>Calcitriol - chemical synthesis</topic><topic>Chemistry Techniques, Synthetic - methods</topic><topic>Convergent synthesis</topic><topic>Monoterpenes - chemical synthesis</topic><topic>Monoterpenes - chemistry</topic><topic>Oxides - chemical synthesis</topic><topic>Oxides - chemistry</topic><topic>Phosphines - chemical synthesis</topic><topic>Phosphines - chemistry</topic><topic>Vitamin D3 metabolites</topic><topic>Vitamins - chemical synthesis</topic><topic>Vitamins - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sigüeiro, Rita</creatorcontrib><creatorcontrib>Otero, Rocio</creatorcontrib><creatorcontrib>González-Berdullas, Patricia</creatorcontrib><creatorcontrib>Loureiro, Julian</creatorcontrib><creatorcontrib>Mouriño, Antonio</creatorcontrib><creatorcontrib>Maestro, Miguel A.</creatorcontrib><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>The Journal of steroid biochemistry and molecular biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sigüeiro, Rita</au><au>Otero, Rocio</au><au>González-Berdullas, Patricia</au><au>Loureiro, Julian</au><au>Mouriño, Antonio</au><au>Maestro, Miguel A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A new approach to 19-nor-A-ring phosphine oxide for the convergent synthesis of 19-nor-calcitriol</atitle><jtitle>The Journal of steroid biochemistry and molecular biology</jtitle><addtitle>J Steroid Biochem Mol Biol</addtitle><date>2017-10</date><risdate>2017</risdate><volume>173</volume><spage>86</spage><epage>88</epage><pages>86-88</pages><issn>0960-0760</issn><eissn>1879-1220</eissn><abstract>•An efficient synthesis of 19-nor-A-ring phospine oxide (5) was achieved from (S)-carvone (7%, 15 steps).•A convergent synthesis of 1α,25-dihydroxy-19-norvitamin D3 (3) was achieved from (S)-carvone and Inhoffen-Lythgoe diol (20 steps, 3%).•The triene system assembly is based on a Wittig-Horner coupling.
[Display omitted]
A new approach to 19-nor-A-ring phosphine oxide 5 together with a convergent synthesis of the vitamin D3 analogue 1α,25-dihydroxy-19-norvitamin D3 (3) have been developed. The 19-nor-A-ring is constructed from (S)-carvone. The triene system is assembled by a Wittig-Horner coupling.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>27592138</pmid><doi>10.1016/j.jsbmb.2016.08.008</doi><tpages>3</tpages><orcidid>https://orcid.org/0000-0001-8922-8033</orcidid></addata></record> |
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| identifier | ISSN: 0960-0760 |
| ispartof | The Journal of steroid biochemistry and molecular biology, 2017-10, Vol.173, p.86-88 |
| issn | 0960-0760 1879-1220 |
| language | eng |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings; MEDLINE |
| subjects | 19-Nor-A-ring phosphine oxide 19-Nor-calcitriol Calcitriol - analogs & derivatives Calcitriol - chemical synthesis Chemistry Techniques, Synthetic - methods Convergent synthesis Monoterpenes - chemical synthesis Monoterpenes - chemistry Oxides - chemical synthesis Oxides - chemistry Phosphines - chemical synthesis Phosphines - chemistry Vitamin D3 metabolites Vitamins - chemical synthesis Vitamins - chemistry |
| title | A new approach to 19-nor-A-ring phosphine oxide for the convergent synthesis of 19-nor-calcitriol |
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