Efficient Solution and Solid-Phase Synthesis of a 3,9-Diazabicyclo[3.3.1]non-6-en-2-one Scaffold

Abstract

The solution and solid-phase syntheses of a 3,9-diazabicyclo[3.3.1]non-6-en-2-one have been realised via sequential Dakin-West/Pictet-Spengler reactions. Scheme 5 Functionalisation of the immobilised scaffold. Reagents and conditions: i) AcCl, Pyridine, CH 2 Cl 2 , 16 h, r.t. ii) BnBr, i-Pr 2 NEt, DMF, 50 °C, 24 h. iii) NaOHaq 2N/H 2 O/THF (2/8/10), r.t., 2 h. Scheme 6 i) 20% TFA/CH 2 Cl 2 , 16 h, r.t.; ii) NaBH 4 , MeOH Downloaded by: Florida International University. Copyrighted material.