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Solution- and Solid-Phase Synthesis of Natural Product-Like Tetrahydroquinoline-Based Polycyclics Having a Medium Size Ring

Abstract : A solid-phase synthesis of tetrahydroquinoline-derived polycyclic 4, having a medium size ring with an enamide functionality, was achieved from tetrahydroquinoline derivative 3 in five steps with overall 40-45% yield. An enantiopure, tetrahydroquinoline-derived beta-amino ester, 1, was converted into compound 2 that has a free phenolic hydroxyl group as an anchoring site for solid-phase synthesis. The solid-phase worked well for this sequence, in which the synthesis of the unsaturated eight-membered enamide lactam was obtained by a ring-closing metathesis approach. Compound 4 is a novel, natural product-like polycyclic derivative that could further be utilized in library generation for developing small molecule chemical probes.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02384488
Contributor : Samuel Couve-Bonnaire <>
Submitted on : Thursday, November 28, 2019 - 1:50:48 PM
Last modification on : Wednesday, April 15, 2020 - 11:26:02 AM

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Prabhat Arya, Samuel Couve-Bonnaire, Patricia Durieux, Daisy Laforce, Rohtash Kumar, et al.. Solution- and Solid-Phase Synthesis of Natural Product-Like Tetrahydroquinoline-Based Polycyclics Having a Medium Size Ring. Journal of Combinatorial Chemistry, American Chemical Society, 2004, 6 (5), pp.735-745. ⟨10.1021/cc049935s⟩. ⟨hal-02384488⟩

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