Stereodivergent synthesis of 2-oxo-oligopyrrolidines by an iterative coupling strategy

Yasuki Soda; Kumpei Tatsumi; Matteo Forner; Shunsei Sato; Kana Shibuya; Tomoe Matagawa; Siro Simizu; Noritaka Chida; Toshitaka Okamura; Takaaki Sato

doi:10.1039/D4OB00350K

Stereodivergent synthesis of 2-oxo-oligopyrrolidines by an iterative coupling strategy†

Yasuki Soda,^a Kumpei Tatsumi,^a Matteo Forner,

^ab Shunsei Sato,^a Kana Shibuya,^a Tomoe Matagawa,^a Siro Simizu,^a Noritaka Chida,

^a Toshitaka Okamura

*^a and Takaaki Sato

*^a

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* Corresponding authors

^a Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama, Japan
E-mail: t-okamura@applc.keio.ac.jp, takaakis@applc.keio.ac.jp

^b Department of Pharmaceutical and Pharmacological Sciences, University of Padova, Via Marzolo, 5, 35131 Padova, PD, Italy

Abstract

Natural linear polyamines play diverse roles in physiological processes by interacting with receptors at the cellular level. Herein, we describe the stereodivergent synthesis of oligopyrrolidines, which are conformationally constrained polyamines. We synthesized dimeric and trimeric 2-oxo-oligopyrrolidines using an iterative coupling strategy. The key to our success is an iridium-catalyzed trans/cis-selective nucleophilic addition and subsequent threo/erythro-stereoselective reduction. The synthesized pyrrolidines show varying cytotoxicities against a human cancer cell line depending on the number of rings and their stereochemistry.

Organic & Biomolecular Chemistry

Stereodivergent synthesis of 2-oxo-oligopyrrolidines by an iterative coupling strategy†

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Stereodivergent synthesis of 2-oxo-oligopyrrolidines by an iterative coupling strategy

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