A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins
3 pages, 2 schemes.-- PMID: 11950346 [PubMed].-- Printed version published Apr 18, 2002.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/ol025580e
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American Chemical Society
2002-03-16
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| Online Access: | http://hdl.handle.net/10261/16770 http://dx.doi.org/10.13039/501100008354 http://dx.doi.org/10.13039/501100008737 |
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dig-ipna-es-10261-167702020-05-23T01:07:13Z A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins Betancor, Carmen Freire, Raimundo Pérez-Martín, Inés Prangé, Thierry Suárez, Ernesto Cooperativa Farmacéutica de Tenerife Dirección General de Investigación Científica y Técnica, DGICT (España) 3 pages, 2 schemes.-- PMID: 11950346 [PubMed].-- Printed version published Apr 18, 2002.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/ol025580e A simple transformation of the eight-carbon side chain of a natural spirostan sapogenin into the cephalostatin north 1 spiroketal moiety is described. This methodology, based on an intramolecular hydrogen abstraction reaction promoted by alkoxy radicals, permits the synthesis of C-22 and C-25 stereoisomers of the dioxaspiro[4.4]nonane cephalostatin ring system. The acid-catalyzed isomerization of the spirocenter in the different isomers is studied. This work was supported by Investigation Programmes BQU2000-0650 and BQU2001-1665 of the Dirección General de Investigación, Spain. I.P.-M. thanks the Cooperativa Farmacéutica de Tenerife (COFARTE), Spain, for a fellowship. 2009-09-09T07:27:06Z 2009-09-09T07:27:06Z 2002-03-16 artículo http://purl.org/coar/resource_type/c_6501 Organic Letters 4(8): 1295-1297 (2002) 1523-7060 http://hdl.handle.net/10261/16770 10.1021/ol025580e http://dx.doi.org/10.13039/501100008354 http://dx.doi.org/10.13039/501100008737 en http://dx.doi.org/10.1021/ol025580e open 2373 bytes 132439 bytes text/plain application/pdf American Chemical Society |
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3 pages, 2 schemes.-- PMID: 11950346 [PubMed].-- Printed version published Apr 18, 2002.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/ol025580e |
| author2 |
Cooperativa Farmacéutica de Tenerife |
| author_facet |
Cooperativa Farmacéutica de Tenerife Betancor, Carmen Freire, Raimundo Pérez-Martín, Inés Prangé, Thierry Suárez, Ernesto |
| format |
artículo |
| author |
Betancor, Carmen Freire, Raimundo Pérez-Martín, Inés Prangé, Thierry Suárez, Ernesto |
| spellingShingle |
Betancor, Carmen Freire, Raimundo Pérez-Martín, Inés Prangé, Thierry Suárez, Ernesto A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins |
| author_sort |
Betancor, Carmen |
| title |
A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins |
| title_short |
A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins |
| title_full |
A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins |
| title_fullStr |
A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins |
| title_full_unstemmed |
A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins |
| title_sort |
convenient synthesis of c-22 and c-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins |
| publisher |
American Chemical Society |
| publishDate |
2002-03-16 |
| url |
http://hdl.handle.net/10261/16770 http://dx.doi.org/10.13039/501100008354 http://dx.doi.org/10.13039/501100008737 |
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