title: Synthesis of fluoroneplanocin A.
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.
authors.affiliation: Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea.
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
authors.forename: Dilip K
authors.initials: DK
authors.lastname: Tosh
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Shantana
authors.initials: S
authors.lastname: Pal
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D043383:Adenosylhomocysteinase / Q000037:antagonists & inhibitors; D003517:Cyclopentanes / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D003517:Cyclopentanes; D004791:Enzyme Inhibitors; C470754:fluoroneplanocin A; D043383:Adenosylhomocysteinase; D000241:Adenosine; C013905:cyclopentenone