Stereocontrolled Solid-Phase Synthesis of a 90-Membered Library of Indoline-Alkaloid-like Polycycles from an Enantioenriched Aminoindoline Scaffold

Zhonghong Gan (1) , P. Thirupathi Reddy (1) , Sophie Quévillon (1) , Samuel Couve-Bonnaire (1) , Prabhat Arya (1)

1 CNRC - Conseil National de Recherches Canada

A library of tricyclic derivatives, similar to indoline alkaloids, has been generated by using a stereocontrolled, conjugate hetero‐Michael approach in both the solution and the solid phase (see scheme; P=protecting group, R=functional group). The mild reaction conditions that lead to the tricyclic derivatives, which contain β‐amino acid functionalities, are highly attractive.

Keywords: combinatorial chemistry; cyclisation; indoline alkaloids; protecting groups; solid-phase synthesis

Domains: Chemical Sciences; Catalysis; Chemical Sciences; Coordination chemistry; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Organic chemistry; Chemical Sciences; Theoretical and/or physical chemistry; Chemical Sciences; Life Sciences [q-bio]; Biochemistry, Molecular Biology; Life Sciences [q-bio]; Cancer; Life Sciences [q-bio]

Zhonghong Gan, P. Thirupathi Reddy, Sophie Quévillon, Samuel Couve-Bonnaire, Prabhat Arya. Stereocontrolled Solid-Phase Synthesis of a 90-Membered Library of Indoline-Alkaloid-like Polycycles from an Enantioenriched Aminoindoline Scaffold. Angewandte Chemie International Edition, 2005, 44 (9), pp.1366-1368. ⟨10.1002/anie.200462298⟩. ⟨hal-02384481⟩