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http://hdl.handle.net/10261/16967
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Campo DC | Valor | Lengua/Idioma |
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dc.contributor.author | Betancor, Carmen | en_US |
dc.contributor.author | Dorta, Rosa L. | en_US |
dc.contributor.author | Freire, Raimundo | en_US |
dc.contributor.author | Martín, Ángeles | en_US |
dc.contributor.author | Prangé, Thierry | en_US |
dc.contributor.author | Suárez, Ernesto | en_US |
dc.date.accessioned | 2009-09-16T10:51:23Z | - |
dc.date.available | 2009-09-16T10:51:23Z | - |
dc.date.issued | 1998-08-07 | en_US |
dc.identifier.citation | Journal of Organic Chemistry 63(18): 6355-6362 (1998) | en_US |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/10261/16967 | - |
dc.description | 8 pages, 1 figure, 5 schemes.-- PMID: 11672270 [PubMed].-- Printed version published Sep 4, 1998. | - |
dc.description | Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo980834o | - |
dc.description.abstract | The reduction of steroidal spiroacetal methanesulfonate derivatives, containing the 1,6-dioxaspiro[4.5]decan-10-yl ring system, with DIBALH promotes a new rearrangement to give steroidal 1,6-dioxadecalin (octahydropyrano[3,2-b]pyran) or 2,2‘-linked ditetrahydrofuran (octahydro[2,2‘]bifuranyl) derivatives. To study the scope and selectivity of the reaction, several steroidal spiroacetals such as (23R,25R)-3β-methoxy-5α-spirostan-23-yl methanesulfonate (2) and its 23S-isomer (5) and (22R,23R,25R)-3β-acetoxy-16β,23:23,26-diepoxycholest-5-en-22-yl methanesulfonate (15) and its 22S-isomer (19) have been synthesized. Compound 2 was rearranged with absolute regio- and stereoselectivity to give (22S,23S,25R)-3β-methoxy-16β,23:22,26-diepoxy-5α-cholestane (3) which possesses a cis-fused 1,6-dioxadecalin ring system. The reaction of compound 5 gave exclusively (22S,23R,25R)-3β-methoxy-23,26-epoxy-5α-furostane (6) in which the spiroacetal was converted into a ditetrahydrofuran subunit. The two other isomeric spiroacetals 15 and 19 were also mainly transformed into (22S,23S,25R)-3β-acetoxy-16β,23:22,26-diepoxycholest-5-ene (16) and (22R,23R,25R)-3β-acetoxy-23,26-epoxyfurost-5-ene (20), respectively. A mechanism is proposed to explain the regio- and sterospecificity observed in the rearrangement. | - |
dc.description.sponsorship | This work was supported by the Investigation Program no. PB96-1461 of the Dirección General de Investigación Científica y Técnica, Spain. A.M. thanks the Ministerio de Educación y Cultura, Spain, for a fellowship. | - |
dc.format.extent | 2373 bytes | - |
dc.format.extent | 1818611 bytes | - |
dc.format.mimetype | text/plain | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | en_US |
dc.publisher | American Chemical Society | - |
dc.rights | closedAccess | en_US |
dc.title | Stereospecific synthesis of 1,6-dioxadecalins and 2,2'-linked ditetrahydrofurans by rearrangement of steroidal spiroacetals | en_US |
dc.type | artículo | en_US |
dc.identifier.doi | 10.1021/jo980834o | - |
dc.relation.publisherversion | http://dx.doi.org/10.1021/jo980834o | - |
dc.contributor.funder | Dirección General de Investigación Científica y Técnica, DGICT (España) | - |
dc.contributor.funder | Ministerio de Educación y Cultura (España) | - |
dc.identifier.funder | http://dx.doi.org/10.13039/501100008737 | es_ES |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.openairetype | artículo | - |
item.grantfulltext | none | - |
item.cerifentitytype | Publications | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.fulltext | No Fulltext | - |
item.languageiso639-1 | en | - |
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