Total Synthesis of (±)-Quinagolide: A Potent D 2 Receptor Agonist for the Treatment of Hyperprolactinemia

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Abstract

A potent dopamine (D 2 ) receptor agonist (±)-quinagolide, which is used for the treatment of hyperprolactinemia, was synthesized using the ring closing metathesis (RCM) approach from meta-hydroxybenzaldehyde as the starting material. The key features of this synthesis are pyrolytic elimination, late-stage expedient synthesis of functionalized trans-fused tetrahydropyridine-3-carboxylates from olefin 6, via conjugate addition-elimination upon acetate 11, followed by RCM and phenyliodine bis(trifluoroacetate) (PIFA)-mediated Hofmann rearrangement of piperidine-3-carboxamide, which enables the synthesis of 3-aminopiperidine skeleton of quinagolide. For the total synthesis of natural products such as ergot alkaloids, late-stage synthesis of functionalized trans-fused tetrahydropyridine-3-carboxylates using RCM and PIFA-mediated Hofmann rearrangement of piperidine-3-carboxamide, which allows quick access to the synthetically challenging 3-aminopiperidine skeleton, are the main achievements of the present work.

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Chavan, S. P., Kadam, A. L., & Kawale, S. A. (2019). Total Synthesis of (±)-Quinagolide: A Potent D 2 Receptor Agonist for the Treatment of Hyperprolactinemia. ACS Omega, 4(5), 8231–8238. https://doi.org/10.1021/acsomega.9b00903

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