N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B

Ye, Zhao-Bao; Chen, Jie; Meng, Wei-Hua; Huang, Pei‐Qiang

doi:10.1016/j.tetasy.2010.04.063

Cited by 11 publications

(1 citation statement)

References 79 publications

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“…The residue was purified by column chromatography on silica gel (40 g, hexanes−EtOAc, 2:1) to give N-Boc-prolyl-iheyanone 6 (632 mg, 70%) as a colorless oil. The ratio of major and minor rotamers was m, 1H), 1.96−1.79 (m, 3H), 1.40 (s, 9H), 1.15 (d, J = 7.3 Hz, 3H), 0.79 (d, J = 6.8 Hz, 3H);13 C NMR (100 MHz, CD 3 OD) for the major rotamer δ 182.0, 173.6, 172.5, 155.8, 95.4, 81.1, 65.5, 61.9, 59.6, 48.0, 31.7, 30.0, 28.7 (3C), 23.5, 19.2, 16.1; HRESIMS m/z 353.2056 [M + H] + (calcd for C 18 H 29 N 2 O 5 353.2071).Active ester 5 used in this reaction was synthesized based on the published procedure 11.…”

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First Total Synthesis and Structure–Activity Relationship of Iheyamide A, an Antitrypanosomal Linear Peptide Isolated from a Dapis sp. Marine Cyanobacterium

et al. 2021

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Iheyamide A (1) is an antitrypanosomal linear peptide isolated from a Dapis sp. marine cyanobacterium by our group in 2020, and based on structure−activity relationships of its natural analogues, the C-terminal pyrrolinone moiety has been identified as the phamacophore for its antiparasitic activity. Further, we isolated this pyrrolinone moiety by itself as a new natural product from the marine cyanobacterium and named it iheyanone (2). As expected, iheyanone (2) showed antitrypanosomal activity, but its potency was weaker than iheyamide A (1). To clarify more detailed structure−activity relationships, we completed a total synthesis of iheyamide A (1) along with iheyanone (2) and evaluated the antitrypanosomal activities of several synthetic intermediates. As a result, we found that the longer the peptide chain, the stronger the antitrypanosomal activity. As iheyamide A (1) showed selective toxicity against Trypanosoma brucei rhodesiense, these findings can provide design guidelines for antitrypanosomal drugs.

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First Total Synthesis and Structure–Activity Relationship of Iheyamide A, an Antitrypanosomal Linear Peptide Isolated from a Dapis sp. Marine Cyanobacterium

et al. 2021

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Synthesis of Pyrrolidones and Caprolactams by Ring Modification or Multi‐component Ring‐Forming Reaction

Chenault

2021

Handbook of Pyrrolidone and Caprolactam Based Materials

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This chapter begins by discussing Lactone‐to‐Lactam Conversion, which is the basis for the commercial manufacture of pyrrolidone and N‐methylpyrrolidone. Multi‐component reactions accomplish the synthesis of pyrrolidones more readily than that of caprolactams. The chapter describes the use of the Beckmann rearrangement, the Schmidt reaction, rearrangement of oxaziridines and rearrangement of a‐azidoketones to synthesize caprolactams and pyrrolidones. The Beckmann rearrangement is the acid‐catalyzed isomerization of an oxime to an amide. The chapter discusses the methods of generating pyrrolidones and caprolactams by partial reduction of cyclic imides or by oxidation of cyclic amines. In multi‐component reactions, two or more molecules come together, forming two or more new sigma bonds and generating a new lactam ring. More complicated versions involve the Ugi reaction. The Ugi reaction involves the condensation of an isocyanide, an aldehyde or ketone, a primary amine and a carboxylic acid to form, ultimately, a structure having two amide linkages, an N‐acyl α‐amino carboxamide.

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Enantioselective Syntheses of Rigidiusculamides A and B: Revision of the Relative Stereochemistry of Rigidiusculamide A

Chen

Huang

et al. 2012

Chemistry An Asian Journal

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The first enantioselective synthesis of cytotoxic natural products rigidiusculamides A (ent-21) and B (8) has been achieved by two synthetic routes. The first one is convergent based on the common intermediate 11, obtained through a high yielding SmI(2) -mediated Reformatsky-type reaction. A highly diastereoselective one-pot Dess-Martin periodinane-mediated bis-oxidation allowed the direct conversion of the diastereomeric mixture of 11 into rigidiusculamide B (8). Isolation of minor diastereomer 21, in combination with computational work, allowed us to suggest the structure of the natural rigidiusculamide A to be ent-21, as synthesized by the second route. Four diastereomers (7, ent-7, 22a, and 22b) and an enantiomer (21) of rigidiusculamide A (ent-21) have been synthesized. On the basis of literature precedents and computational work, a biosynthetic pathway for rigidiusculamides A and B was proposed to account for the opposite configuration at C-5 of those two congeners.

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N-Benzyloxymalimide for an easy access to 5-alkyl-3-pyrrolin-2-ones: asymmetric synthesis of the mixed imide substructure of the potent immunosuppressant microcolin B

Cited by 11 publications

References 79 publications

First Total Synthesis and Structure–Activity Relationship of Iheyamide A, an Antitrypanosomal Linear Peptide Isolated from a Dapis sp. Marine Cyanobacterium

First Total Synthesis and Structure–Activity Relationship of Iheyamide A, an Antitrypanosomal Linear Peptide Isolated from a Dapis sp. Marine Cyanobacterium

Synthesis of Pyrrolidones and Caprolactams by Ring Modification or Multi‐component Ring‐Forming Reaction

Enantioselective Syntheses of Rigidiusculamides A and B: Revision of the Relative Stereochemistry of Rigidiusculamide A

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