Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids

PILAR VENTOSA-ANDRES; AGUSTINA LA VENIA; CARLOS A BAREA RIPOLL; LUDMILA HRADILOVA; VIKTOR KRCHNAK

Chemistry - A European Journal

Wiley-VCH

Año: 2015 vol. 21 p. 13112 - 13119

Herein, we describe thesynthesis of molecular scaffolds consisting of medium-sized fused heterocyclesusing amino acids, which are some of the most useful building blocks used bynature as well as chemists to create structural diversity. The acyclic precursorswere assembled using traditional Merrifield solid-phase peptide synthesis, andcyclization was carried out via acid-mediated tandem endocyclic N-acyliminium ions, followed bynucleophilic addition with internal nucleophiles. The synthesis of molecular scaffolds consisting of seven-, eight-, and nine-membered rings proceeded withfull stereocontrol of the newly generated stereogenic center in most cases.