Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

Tamura, Osamu; Ueda, Tohru; Inada, Mitsuhide; Morita, Nobuyoshi

doi:10.3987/com-14-s(k)93

HETEROCYCLES

2015

DOI: 10.3987/com-14-s(k)93

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Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

Osamu Tamura¹,

Tohru Ueda²,

Mitsuhide Inada³

et al.

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Cited by 6 publications

References 45 publications

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Spiro‐2‐oxindoles via 1,3‐dipolar cycloadditions. A decade update

Molteni

Silvani

2021

Eur J Org Chem

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The great variety of spirooxindole three‐dimensional scaffolds encompasses relevant bioactive natural alkaloids as well as useful therapeutic agents. In view of the challenging features of the spirooxindole skeletons and their desirable properties, several synthetic routes have been devoted to their preparation. Because of the variety of both 1,3‐dipolar species and 2‐oxindoles bearing a C=X double bond (X=C<, N−, O) in the 3‐position, a prominent role relies upon a 1,3‐dipolar cycloaddition as the key step of the whole synthetic sequence. The present paper aims to discuss the developments in the field of spirooxindole synthesis via a 1,3‐dipolar cycloaddition occurred in the 2011–2020 decade. The literature data on this subject are reviewed in a systematic way according to the type of the 1,3‐dipole and the oxindole dipolarophile.

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Spiro‐2‐oxindoles via 1,3‐dipolar cycloadditions. A decade update

Molteni

Silvani

2021

Eur J Org Chem

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Synthesis of 3‐Hydroxy‐2‐oxindole and 2,5‐Diketopiperazine Cores as Privileged Scaffolds of Indole Alkaloids

Karpe

Mondal

2022

ChemistrySelect

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The diverse biological activities of synthetically and naturally occurring molecules containing functionalized 2,5-diketopiperazines and/or 3-hydroxy-2-oxindoles have sparked an interest in medicinal chemistry. This paper describes the Barbier reaction-mediated synthesis of 3-substituted-3-hydroxy-2-oxindole from commercially available isatin and the construction of spiro-epoxy-2-oxindole via (E)-selective olefin installation at the C3-position of N-methylisatin followed by epoxidation reaction.It also includes the formation of 2,5-diketopiperazine scaffolds from amino acid derivatives via amide coupling reaction. The synthesis of these "privileged cores" has been reported herein as key precursors to the accessibility of several complex alkaloid series of natural products, such as maremycins and other structurally related and medicinally significant natural and their synthetic analogues.

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Concise Synthesis of 2,5-Diketopiperazines via Catalytic Hydroxy-Directed Peptide Bond Formations

et al. 2023

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2,5-Diketopiperazines (DKPs) with hydroxymethyl functional groups are essential structures found in many bioactive molecules and functional materials. We have established a simple protocol for the concise synthesis of this type of DKPs through diboronic acid anhydride-catalyzed hydroxy-directed peptide bond formations. The sequential reactions in this report, which consist of three steps, an intermolecular catalytic condensation reaction in which water is the only byproduct, a simple deprotection of the nitrogen-protecting group, and an intramolecular cyclization, enabled the synthesis of functionalized DKPs in high to excellent yields without any intermediate purification. The utility of this protocol has been demonstrated by synthesizing natural products, phomamide and Cyclo(Deala-L-Leu).

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Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

Cited by 6 publications

References 45 publications

Spiro‐2‐oxindoles via 1,3‐dipolar cycloadditions. A decade update

Spiro‐2‐oxindoles via 1,3‐dipolar cycloadditions. A decade update

Synthesis of 3‐Hydroxy‐2‐oxindole and 2,5‐Diketopiperazine Cores as Privileged Scaffolds of Indole Alkaloids

Concise Synthesis of 2,5-Diketopiperazines via Catalytic Hydroxy-Directed Peptide Bond Formations

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