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T3P-promoted, mild one-pot syntheses of constrained polycyclic lactam dipeptide analogues via stereoselective Pictet-Spengler and Meyers’ lactamization reactions.

  • August 31, 2015

A new convenient, mild, one-pot procedure is described for the diastereoselective synthesis of constrained 7,5- and 7,6-fused azabicycloalkanes. Using 2-formyl-L-tryptophan and 2-formyl-l-phenylalanine as bielectrophilic building blocks, T3P-mediated Pictet–Spengler and Meyers lactamization reactions were developed to present chiral and polycyclic aminoindolo- and aminobenzazepinone compounds in excellent yields. The conformationally constrained compounds can serve as templates for peptidomimetic research or polyheterocyclic privileged scaffolds.

 

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