By an efficient and mild diastereoselective aldol-type reaction of aromatic aldehyde with 4-methoxyfuran-2(5H)-one, losigamone and a series of its analogues were synthesized. Fortunately, the racemic threo-isomers of losigamone were obtained by crystallization with good de value (≥96%). The introduction of chiral reagents to the reaction system resulted in diastereoselectivity to losigamone. All structures of new compounds were confirmed by 1 H NMR, 13 C NMR, IR and HRMS techniques.
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