Herein, we describe the synthesis of molecular scaffolds consisting of medium-sized fused heterocycles using amino acids, which are some of the most useful building blocks used by nature as well as chemists to create structural diversity. The acyclic precursors were assembled by using traditional Merrifield solid-phase peptide synthesis, and cyclization was carried out through acid-mediated tandem endocyclic N-acyliminium ion formation, followed by nucleophilic addition with internal nucleophiles. The synthesis of molecular scaffolds consisting of seven-, eight-, and nine-membered rings proceeded with full stereocontrol of the newly generated stereogenic center in most cases.

Department of Chemistry and Biochemistry University of Notre Dame 251 Nieuwland Science Center Notre Dame Indiana 46556

Department of Organic Chemistry Palacky University771 46 Olomouc

Farmak Na vlčinci 16 3 Klášterní Hradisko 779 00 Olomouc 251

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Traceless Solid-Phase Synthesis of [6,7,8 + 5,6,7]-Fused Molecular Frameworks