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Catalytic reduction of known (R/S)-, (R)-, and (S)-2-nitro-N-(1-phenylethyl)benzamides 20-2237,38 prepared by standard methods afforded the corresponding (R/S)-,37 (R)-, and (S)-2-aminobenzamides 23-25, which were in turn condensed with 2-hydroxy-1-naphtaldehyde in acidic medium to give sirtinol 1 and (R)- and (S)-sirtinol, 9 and 10 respectively (Scheme 3).
General procedure: A mixture of isatoic anhydride (1 mmol), amine (1 mmol), and aromatic aldehyde (1 mmol) in H2O (5 mL) was stirred at room temperature for 2-3 h. After the completion of reaction (checked by TLC), the precipitate was filtered off and recrystallized from ethanol to give the pure compound 6