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A convenient synthesis of C-22 and C-25 stereoisomers of cephalostatin north 1 side chain from spirostan sapogenins

AuthorsBetancor, Carmen; Freire, Raimundo ; Pérez-Martín, Inés ; Prangé, Thierry; Suárez, Ernesto
Issue Date16-Mar-2002
PublisherAmerican Chemical Society
CitationOrganic Letters 4(8): 1295-1297 (2002)
AbstractA 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.
Description3 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
Publisher version (URL)http://dx.doi.org/10.1021/ol025580e
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