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Synthesis of fluoroneplanocin A.

Lak Shin Jeong1, Dilip K Tosh, Won Jun Choi

  • 1Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea.

Current Protocols in Nucleic Acid Chemistry
|September 27, 2008
PubMed
Summary

Fluoroneplanocin A, an irreversible inhibitor of S-adenosylhomocysteine hydrolase (SAH), is synthesized from D-ribose. Key steps include stereoselective Grignard and ring-closing metathesis reactions for a crucial intermediate.

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Area of Science:

  • Organic Synthesis
  • Medicinal Chemistry
  • Biochemistry

Background:

  • S-adenosylhomocysteine hydrolase (SAH) is a critical enzyme in cellular metabolism.
  • Inhibitors of SAH are of interest for therapeutic applications.
  • Fluoroneplanocin A is a designed mechanism-based irreversible inhibitor of SAH.

Purpose of the Study:

  • To outline the synthetic route for Fluoroneplanocin A.
  • To detail the key chemical transformations involved in synthesizing a D-cyclopentenone intermediate.

Main Methods:

  • Synthesis initiated from D-ribose.
  • Key intermediate synthesized via stereoselective Grignard reaction.
  • Ring-closing metathesis (RCM) and oxidative rearrangement employed.

Main Results:

  • Successful synthesis of Fluoroneplanocin A.
  • Demonstration of efficient stereoselective synthesis of the D-cyclopentenone intermediate.
  • Validation of RCM and oxidative rearrangement as key steps.

Conclusions:

  • Fluoroneplanocin A can be synthesized effectively from D-ribose.
  • The synthetic strategy highlights the utility of stereoselective Grignard and RCM reactions.
  • This synthesis provides a pathway to a potent SAH inhibitor.