Catalyst-free synthesis of borodepsipeptides using isocyano arylboronate under aqueous condition
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Catalyst‑free synthesis of borodepsipeptides using isocyano arylboronate under aqueous condition Yao‑Yu Chiang1 · Yi‑Chen Kuo1 · Sung‑Chi Lin1 · Pei‑Yin Yeh1 · Yi‑Wei Chen2 · Po‑Shen Pan1 Received: 26 March 2020 / Accepted: 28 July 2020 © Springer Nature B.V. 2020
Abstract Herein, the synthesis of borodepsipeptides utilizing boron-containing isocyanides is described. The target compounds were synthesized via Passerini three-component reaction (P-3CR), in which H2O was utilized as the solvent. Further, unlike conventional P-3CR, where Lewis acid catalysts are often required, the reported method requires no catalyst and proceeds in room temperature. A variety of aldehydes and acids were used as the building blocks to generate the desired products. Keywords No catalyst · Room temperature · Passerini · Isocyano-boronate esters · Multicomponent reaction
Introduction Multicomponent reaction (MCR) is a powerful synthetic strategy that converts three or more starting materials to a single product in one-pot fashion. It also makes a great contribution in medicinal chemistry, in which diverse biological active molecules could be generated. Depsipeptides are unique class compounds that often appear in wide spectrum of natural products and pharmaceuticals. These products often possess invaluable biological properties such as antitumor and anti-inflammatory activities [1, 2]. The isocyanide-based multicomponent reaction (IMCR), such as P-3CR) [3, 4], provides a straightforward strategy to construct compounds with depsipeptide scaffold. This reaction has been widely used for making natural products [5], peptide mimetics [6] and heterocyclic/heteroaromatic carboxylic ester derivatives [7]. Boron-containing analogous has drawn significant attention in medicinal chemistry due to * Po‑Shen Pan [email protected] 1
Department of Chemistry, Tamsui Dist, Tamkang University, No. 151 Yingzhuan rd, New Taipei City 25137, Taiwan
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Department of Oncology, Taipei Veterans General Hospital, Taipei City, Taiwan
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its distinctive capability of forming a reversible covalent bonding with its biological targets [8]. For the past decade, synthetic efforts for making such entities have been widely discussed [9, 10]. In the last decade, reports regarding the utilization of P-3CR to produce boron-containing depsipeptides have been published [11, 12]. Although P-3CR is so-called isocyanide-based MCR, these reports are mainly focusing on having boron-containing carboxylic acids or aldehydes as the only building blocks. This is partly due to the fact that boron-containing isocyanides are generally perceived as the unstable materials that are not suitable for synthetic applications. However, our previous report has shown that isocyano arylboronates are quite stable and could be used as the stable synthetic building blocks [13]. Herein, we report the use of such building block in P-3CR to construct a series of boron-containing depsipeptide analogues.
Materials and methods
2-oxo-1-phenyl-2-((4-(4,
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