Literature DB >> 10986072

A short formal synthesis of squalamine from a microbial metabolite.

W A Kinney1, X Zhang, J I Williams, S Johnston, R S Michalak, M Deshpande, L Dostal, J P Rosazza.   

Abstract

A short formal synthesis of squalamine is described, utilizing the biotransformation product 2, which is available in one step from commercially available 3-keto-23,24-bisnorchol-4-en-22-ol (1). Regioselective C-22 oxidation and C-24 sulfation of the corresponding alcohols in the presence of a free C-7 alcohol make for an efficient preparation of squalamine intermediate 11.

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Year:  2000        PMID: 10986072     DOI: 10.1021/ol0059495

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


  2 in total

1.  Access to functionalized steroid side chains via modified Julia olefination.

Authors:  Enver Cagri Izgu; Aaron C Burns; Thomas R Hoye
Journal:  Org Lett       Date:  2011-01-18       Impact factor: 6.005

Review 2.  From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues.

Authors:  Oxana Kazakova; Gulnara Giniyatullina; Denis Babkov; Zdenek Wimmer
Journal:  Int J Mol Sci       Date:  2022-01-19       Impact factor: 5.923

  2 in total

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