(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate → (3aR,4R,5R,6aS)-2-oxo-4-(3-oxo-4-phenoxybutyl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate
Reaction equation
[C:1]([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@H:11]1/[CH:19]=[CH:20]/[C:21](=[O:30])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[C:1]([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@H:11]1[CH2:19][CH2:20][C:21](=[O:30])[CH2:22][O:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
(3aR,4R,5R,6aS)-2-Oxo-4-((E)-3-oxo-4-phenoxybut-1-enyl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate, prepared in Step A, is dissolved in ethyl acetate and 10% Pd/C is added to the solution under a nitrogen atmosphere. The solution is flushed with hydrogen gas and subsequently stirred under a hydrogen atmosphere until starting material is consumed as judged by TLC. The crude reaction mixture is filtered through Celite and the solvent is removed under reduced pressure. The crude product is purified by flash chromatography on regular silica gel eluted with ethyl acetate-hexanes to afford the title intermediate.