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Synthesis of 1-deoxysphingosine derivatives with conformationally restricted pyrrolidinediol head groups.

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.

SUBMITTER: Dougherty AM

PROVIDER: S-EPMC4604444 | biostudies-literature | 2006 Feb

REPOSITORIES: biostudies-literature

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Synthesis of 1-deoxysphingosine derivatives with conformationally restricted pyrrolidinediol head groups.

Dougherty Ann M AM McDonald Frank E FE Liotta Dennis C DC Moody Steven J SJ Pallas David C DC Pack Carrie D CD Merrill Alfred H AH

Organic letters 20060201 4

[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 ...[more]

PMID: 16468733

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