Literature DB >> 11950346

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

Carmen Betancor1, Raimundo Freire, Inés Pérez-Martín, Thierry Prangé, Ernesto Suárez.   

Abstract

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. [reaction: see text]

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Year:  2002        PMID： 11950346     DOI： 10.1021/ol025580e

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

Review 1.  Recent progress of isocyanide-based multicomponent reactions in Iran.

Authors:  Ahmad Shaabani; Ali Maleki; Ali Hossein Rezayan; Afshin Sarvary
Journal:  Mol Divers       Date:  2010-07-29       Impact factor: 2.943

Review 2.  Chemistry of trisdecacyclic pyrazine antineoplastics: the cephalostatins and ritterazines.

Authors:  Seongmin Lee; Thomas G LaCour; Philip L Fuchs
Journal:  Chem Rev       Date:  2009-06       Impact factor: 60.622

3.  Synthesis of an A'B' Precursor to Angelmicin B: Product Diversification in the Suárez Lactol Fragmentation.

Authors:  Jialiang Li; Louis Todaro; David R Mootoo
Journal:  European J Org Chem       Date:  2011-09-07

4.  Synthesis of C14,15-dihydro-C22,25-epi north unit of cephalostatin 1 via "red-ox" modifications of hecogenin acetate.

Authors:  Seongmin Lee; Daniel Jamieson; Philip L Fuchs
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

5.  Synthesis of the AB subunit of angelmicin B through a tandem alkoxy radical fragmentation-etherification sequence.

Authors:  Jialiang Li; Louis J Todaro; David R Mootoo
Journal:  Org Lett       Date:  2008-03-07       Impact factor: 6.005

Review 6.  Chemical and enzymatic approaches to carbohydrate-derived spiroketals: di-D-fructose dianhydrides (DFAs).

Authors:  M Isabel García-Moreno; Juan M Benito; Carmen Ortiz Mellet; José M García Fernández
Journal:  Molecules       Date:  2008-08-12       Impact factor: 4.411
  6 in total

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