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 language | English |
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Pages (from-to) | 14.6.1-14.6.18 |
Journal | Current Protocols in Nucleic Acid Chemistry |
Issue number | SUPPL. 34 |
DOIs | |
State | Published - 2008 |
Keywords
- Electrophilic vinyl fluorination
- Fluoroneplanocin A
- Oxidative rearrangement
- Ring-closing metathesis
- S-adenosylhomocysteine hydrolase