Short Synthesis of New 23-Vinyl Steroid Derivatives from Sapogenins by the Action of 9-BBN on Vinylogous Esters
Some new 16β‐acetoxy‐22,26‐epoxy‐23‐vinylcholest‐22‐ene steroid derivatives have been synthesized from sapogenins via a two‐step sequence involving the reduction of a vinylogous ester moiety by 9‐BBN, a reaction with few precedents and for which a coherent mechanistic interpretation has not been giv...
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| Veröffentlicht in: | European journal of organic chemistry 2004-08, Vol.2004 (15), p.3262-3268 |
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| container_end_page | 3268 |
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| container_issue | 15 |
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| container_title | European journal of organic chemistry |
| container_volume | 2004 |
| creator | Sandoval-Ramírez, Jesús Meza-Reyes, Socorro del Rio, Rosa E. Vazques, Fabiola Reyes Santillán, Rosa Luisa Achab, Said Bohé, Luis |
| description | Some new 16β‐acetoxy‐22,26‐epoxy‐23‐vinylcholest‐22‐ene steroid derivatives have been synthesized from sapogenins via a two‐step sequence involving the reduction of a vinylogous ester moiety by 9‐BBN, a reaction with few precedents and for which a coherent mechanistic interpretation has not been given before now. Some mechanistic insight into this reaction was gained from NMR spectroscopic evidence. A plausible general mechanistic interpretation of the action of 9‐BBN on vinylogous esters is proposed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004) |
| doi_str_mv | 10.1002/ejoc.200400178 |
| format | Article |
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KGaA, 69451 Weinheim, Germany, 2004)</description><subject>23-Vinyl-22</subject><subject>23‐Vinyl‐22,26‐epoxycholest‐22‐enes</subject><subject>26-epoxycholest-22-enes</subject><subject>9-BBN</subject><subject>Sapogenins</subject><subject>Spiroketal cleavage</subject><subject>Vinylogous esters</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNqFkEtPAjEUhRujiYhuXfcPFPuYV5cwIEpwXIwPdk2ndKAIU9KO4Px7BzHEnat7Fvf7knMAuCW4RzCmd3plVY9iHGBM4uQMdAjmHOGI4_M2ByxAhLPZJbjyfoUx5lFEOsDmS-tqmDdVvdTeeGhLmOk9pAy9mapZw7zWzpo5HGpndrI2O-1h6ewG5nJrF7oylYdFA1sa9lVtbHUwcDQYZLDNPw67sJ8ejnxr8tfgopRrr29-bxe83o9e0gc0fR4_pv0pUoyGCSIJLZSOMGNMlpKSuFBBSRgOuC6jOIySgBdts2KuVFBIRjUt5lGSxHIex1SrkHVB7-hVznrvdCm2zmykawTB4jCXOMwlTnO1AD8Ce7PWzT_fYjR5Tv-y6MiatuPXiZXuQ0Qxi0Pxno1FNhykk1lIxBP7BpSnfm4</recordid><startdate>200408</startdate><enddate>200408</enddate><creator>Sandoval-Ramírez, Jesús</creator><creator>Meza-Reyes, Socorro</creator><creator>del Rio, Rosa E.</creator><creator>Vazques, Fabiola Reyes</creator><creator>Santillán, Rosa Luisa</creator><creator>Achab, Said</creator><creator>Bohé, Luis</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200408</creationdate><title>Short Synthesis of New 23-Vinyl Steroid Derivatives from Sapogenins by the Action of 9-BBN on Vinylogous Esters</title><author>Sandoval-Ramírez, Jesús ; Meza-Reyes, Socorro ; del Rio, Rosa E. ; Vazques, Fabiola Reyes ; Santillán, Rosa Luisa ; Achab, Said ; Bohé, Luis</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3258-182bce60333afa217bc4f13049ef6756849b069bdcc4ba32e2bd6887ad772ec53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>23-Vinyl-22</topic><topic>23‐Vinyl‐22,26‐epoxycholest‐22‐enes</topic><topic>26-epoxycholest-22-enes</topic><topic>9-BBN</topic><topic>Sapogenins</topic><topic>Spiroketal cleavage</topic><topic>Vinylogous esters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sandoval-Ramírez, Jesús</creatorcontrib><creatorcontrib>Meza-Reyes, Socorro</creatorcontrib><creatorcontrib>del Rio, Rosa E.</creatorcontrib><creatorcontrib>Vazques, Fabiola Reyes</creatorcontrib><creatorcontrib>Santillán, Rosa Luisa</creatorcontrib><creatorcontrib>Achab, Said</creatorcontrib><creatorcontrib>Bohé, Luis</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sandoval-Ramírez, Jesús</au><au>Meza-Reyes, Socorro</au><au>del Rio, Rosa E.</au><au>Vazques, Fabiola Reyes</au><au>Santillán, Rosa Luisa</au><au>Achab, Said</au><au>Bohé, Luis</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Short Synthesis of New 23-Vinyl Steroid Derivatives from Sapogenins by the Action of 9-BBN on Vinylogous Esters</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. 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| ispartof | European journal of organic chemistry, 2004-08, Vol.2004 (15), p.3262-3268 |
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| language | eng |
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| source | Access via Wiley Online Library |
| subjects | 23-Vinyl-22 23‐Vinyl‐22,26‐epoxycholest‐22‐enes 26-epoxycholest-22-enes 9-BBN Sapogenins Spiroketal cleavage Vinylogous esters |
| title | Short Synthesis of New 23-Vinyl Steroid Derivatives from Sapogenins by the Action of 9-BBN on Vinylogous Esters |
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