Synthesis of fluoroneplanocin A

Lak Shin Jeong, Dilip K. Tosh, Won Jun Choi, Shantana Pal

Research output: Contribution to journalReview articlepeer-review

Abstract

Fluoroneplanocin A, designed as a potent mechanism-based irreversible inhibitor of S-adenosylhomocysteine hydrolase (SAH), is synthesized from D-ribose via a key D-cyclopentenone intermediate. This intermediate is synthesized using a stereoselective Grignard reaction, a ring-closing metathesis (RCM) reaction, and oxidative rearrangement as key steps.

Original languageEnglish
Pages (from-to)14.6.1-14.6.18
JournalCurrent Protocols in Nucleic Acid Chemistry
Issue numberSUPPL. 34
DOIs
StatePublished - 2008

Keywords

  • Electrophilic vinyl fluorination
  • Fluoroneplanocin A
  • Oxidative rearrangement
  • Ring-closing metathesis
  • S-adenosylhomocysteine hydrolase

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