Synthesis of 1-deoxysphingosine derivatives with conformationally restricted pyrrolidinediol head groups |
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Authors: | Dougherty Ann M McDonald Frank E Liotta Dennis C Moody Steven J Pallas David C Pack Carrie D Merrill Alfred H |
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Institution: | Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA. |
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Abstract: | structure: see text] A family of cyclic 1-deoxysphingolipid derivatives of structure 4 has been designed and synthesized, which may serve as tumorigenesis suppressors for various cancers. Compound 4 is a second-generation analogue developed from sphingosine (1), in which a hydroxyl substituent is moved from C1 to C5 and a methylene is added for conformational rigidity between the C2-nitrogen substituent and C4. The synthetic chemistry for pyrrolidine ring closure at C3-C4 features ring-closing metathesis followed by hydroboration-oxidation. |
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