Furan Approach to Vitamin D Analogues. Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D3
The A-rings of calcitriol (1α,25-dihydroxyvitamin D3) and 1α-hydroxy-3-deoxyvitamin D3 were synthesized using the furan approach. The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsil...
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| Veröffentlicht in: | Journal of organic chemistry 2010-10, Vol.75 (20), p.6820-6829 |
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| container_end_page | 6829 |
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| container_issue | 20 |
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| container_title | Journal of organic chemistry |
| container_volume | 75 |
| creator | Miles, William H Connell, Katelyn B Ulas, Gözde Tuson, Hannah H Dethoff, Elizabeth A Mehta, Varun Thrall, April J |
| description | The A-rings of calcitriol (1α,25-dihydroxyvitamin D3) and 1α-hydroxy-3-deoxyvitamin D3 were synthesized using the furan approach. The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)propanal, a diastereoselective Friedel−Crafts hydroxyalkylation, an oxidation of the 2,3-disubstituted furan to give a γ-hydroxybutenolide, and a Peterson olefination. The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield. |
| doi_str_mv | 10.1021/jo101155c |
| format | Article |
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The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo101155c</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties ; Steroids</subject><ispartof>Journal of organic chemistry, 2010-10, Vol.75 (20), p.6820-6829</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo101155c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo101155c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23325529$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Miles, William H</creatorcontrib><creatorcontrib>Connell, Katelyn B</creatorcontrib><creatorcontrib>Ulas, Gözde</creatorcontrib><creatorcontrib>Tuson, Hannah H</creatorcontrib><creatorcontrib>Dethoff, Elizabeth A</creatorcontrib><creatorcontrib>Mehta, Varun</creatorcontrib><creatorcontrib>Thrall, April J</creatorcontrib><title>Furan Approach to Vitamin D Analogues. 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Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D3</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2010-10-15</date><risdate>2010</risdate><volume>75</volume><issue>20</issue><spage>6820</spage><epage>6829</epage><pages>6820-6829</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The A-rings of calcitriol (1α,25-dihydroxyvitamin D3) and 1α-hydroxy-3-deoxyvitamin D3 were synthesized using the furan approach. The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)propanal, a diastereoselective Friedel−Crafts hydroxyalkylation, an oxidation of the 2,3-disubstituted furan to give a γ-hydroxybutenolide, and a Peterson olefination. 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| source | ACS Publications |
| subjects | Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Organic chemistry Preparations and properties Steroids |
| title | Furan Approach to Vitamin D Analogues. Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D3 |
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