title: Synthesis of neplanocin A and its 3'-epimer via an intramolecular Baylis-Hillman reaction.
abstract: The key cyclopentenyl intermediate 11b was synthesized in 4 steps from d-ribose in 41% overall yield via an efficient intramolecular Baylis-Hillman reaction. This novel key intermediate can be modified easily and transformed to neplanocin A (1a) and its 3'-epimer (1b).
authors.affiliation: Institute of Chemical & Engineering Sciences, A*STAR (Agency for Science, Technology and Research) , 8 Biomedical Grove, Neuros#07-01, Singapore 13866.
authors.forename: Yun Xuan
authors.initials: YX
authors.lastname: Tan
authors.forename: Sridhar
authors.initials: S
authors.lastname: Santhanakrishnan
authors.forename: Hai Yan
authors.initials: HY
authors.lastname: Yang
authors.forename: Christina L L
authors.initials: CL
authors.lastname: Chai
authors.forename: Eric Kwok Wai
authors.initials: EK
authors.lastname: Tam
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003517:Cyclopentanes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; C031096:neplanocin A; D000241:Adenosine