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1 article(s) from Beller, Marc Paul

Vicinal ketoesters – key intermediates in the total synthesis of natural products

Marc Paul Beller and
Ulrich Koert

Beilstein J. Org. Chem. 2022, 18, 1236–1248, doi:10.3762/bjoc.18.129

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Graphical Abstract

Scheme 1: Structures of vicinal ketoesters and examples for their typical reactivity.

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Scheme 2: Doyle’s diastereoselective intramolecular aldol addition of α,β-diketoester.

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Scheme 3: Synthesis of euphorikanin A (16) by intramolecular, nucleophilic addition [6].

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Scheme 4: Ketoester cycloisomerization for the synthesis of preussochromone A (24) [10].

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Scheme 5: Diastereoselective, intramolecular aldol reaction of an α-ketoester 28 in the synthesis of (−)-preu...

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Scheme 6: Synthesis of an α-ketoester through Riley oxidation and its use in an α-ketol rearrangement in the ...

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Scheme 7: Azomethine imine cycloaddition towards the synthesis of the proposed structure of palau’amine (44) [19]....

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Scheme 8: Intramolecular diastereoselective carbonyl-ene reaction of an α-ketoester in the synthesis of jatro...

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Scheme 9: Grignard addition to an α-ketoester and subsequent Friedel–Crafts cyclization in the synthesis of (...

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Scheme 10: Diastereoselective addition to an auxiliary modified α-ketoester in the formal synthesis of (+)-cam...

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Scheme 11: Intramolecular photoreduction of an α-ketoester in the synthesis of (rac)-isoretronecanol (69) [26].

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Scheme 12: α-Ketoester as nucleophile in a Tsuji–Trost reaction in the synthesis of (rac)-corynoxine (76) [27].

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Scheme 13: Mannich reaction of an α-ketoester in the synthesis of (+)-gracilamine (83) [28].

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Scheme 14: Enantioselective aldol reaction using an α-ketoester in the synthesis of (−)-irofulven (87) [29].

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Scheme 15: Allylboration of a mesoxalic acid ester in the synthesis of (+)-awajanomycin (92) [30,31].

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Scheme 16: Condensation of a diamine with mesoxolate in the synthesis of (−)-aplaminal (96) [32].

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Scheme 17: Synthesis of mesoxalic ester amide 102 and its use in the synthesis of (rac)-cladoniamide G (103) [33].

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Scheme 18: The thermodynamically controlled, intramolecular aldol addition of a vic-tricarbonyl compound in th...

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Review

Published 15 Sep 2022

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