Synthesis of Novel Fluoranthene-Based Conformationally Constrained α-Amino Acid Derivatives and Polycyclic Aromatics via the Diels–Alder Reaction

Abstract

Conformationally constrained cyclic α-amino acid moieties have been fused to the fluoranthene system. Aminoindanecarboxylic acid (Aic) and 1,2,3,4-tetrahydroisoquinolinecarboxylic acid (Tic) derivatives were synthesized by an alkylation sequence, whereas a aminotetralincarboxylic acid (Atc) derivative was assembled using the Diels–Alder reaction as a key step. These α-amino acid derivatives are considered as constrained analogues of phenylalanine (Phe) and play an important role in the design and synthesis of bioactive peptides and some fluorescence chemosensor molecules. Moreover, this strategy has been extended to polycyclic aromatics via the Diels–Alder reaction and subsequent aromatization with DDQ.

Key words

amino acids - alkylation - bioorganic chemistry - fused-ring systems - Diels–Alder reaction

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