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Author Notes:

Correspondence to: Frank E. McDonald, fmcdona@emory.edu; Dennis C. Liotta, dliotta@emory.edu.

Subjects:

Research Funding:

This research was supported by the National Institutes of Health, through the National Cooperative Drug Discovery Grant program U19 CA 87525, and R01 CA 57327 to D. C. P.

Keywords:

  • Science & Technology
  • Physical Sciences
  • Chemistry, Organic
  • Chemistry
  • RING-CLOSING METATHESIS
  • ASYMMETRIC-SYNTHESIS
  • AMINES
  • SPHINGOSINE
  • INHIBITION
  • EFFICIENT
  • IMINES
  • CELLS
  • BASES

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

Tools:

Journal Title:

Organic Letters

Volume:

Volume 8, Number 4

Publisher:

, Pages 649-652

Type of Work:

Article | Post-print: After Peer Review

Abstract:

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.

Copyright information:

© 2006 American Chemical Society.

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