Butenolide annelation using a manganese(III) oxidation. A synthesis of 4-arylfuran-2(5H)-ones

Date

1999-02-19

Author

Demir, Ayhan Sıtkı
Camkerten, N
Gercek, Z
Duygu, N
Reis, O
Arikan, E

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

158
views

0
downloads

A general procedure was developed for the annelation of a butenolide to an aromatic ketone that highlighted a manganese(III) oxidation of aromatic ketones. The oxidation of aromatic ketones with manganese(III) acetate in the presence of 2;bromoacetic acid or the Mn(II) salt of this carboxylic acid provided a regioselectively convenient synthesis of 2-(2-bromoacetoxy) ketones. An Arbuzov or Wittig reaction of 2-(2-bromoacetoxy) ketones followed by cyclisation furnished 4-arylfuran-2(5H)-ones in good yield. (C) 1999 Elsevier Science Ltd. Ail rights reserved.

Subject Keywords

Carboxylic-Acids, Facile Synthesis, Acetate, 2-Cyclohexenones, Combination, Ketones

URI

https://hdl.handle.net/11511/56480

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/s0040-4020(99)00036-8

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

BUTENOLIDE ANNELATIONS USING A MANGANESE(III) OXIDATION - A SYNTHESIS OF JOLKINOLIDE-E DEMIR, AS; Tanyeli, Cihangir; AKGUN, H; CALISKAN, Z; OZGUL, E (1995-01-01) A general procedure was developed for the annelation of a butenolide to an enone that highlighted a manganese(III) oxidation of an enone. The merit of this procedure was illustrated in a synthesis of (-)-jolkinolide E, ent-1, from (+)-manool 11. A potassium permanganate-mediated degradation of 11 and dehydration of an intermediate beta-hydroxyketone 12 according to a literature procedure afforded a tricyclic enone 13. Oxidation of 13 with manganese(III) acetate and chloropropionic acid regio- and stereosele...
Benzoylformate decarboxylase from Pseudomonas putida as stable catalyst for the synthesis of chiral 2-hydroxy ketones Iding, H; Dunnwald, T; Greiner, L; Liese, A; Muller, M; Siegert, P; Grotzinger, J; Demir, Ayhan Sıtkı; Pohl, M (2000-04-14) The thiamin diphosphate- and Mg2+-dependent enzyme benzoylformate decarboxylase (BFD) from Pseudomonas putida was characterized with respect to its suitability to catalyze the formation of chiral 2-hydroxy ketones in a benzoin-condensation type reaction. Carboligation constitutes a side reaction of BFD, whereas the predominant physiological task of the enzyme is the non-oxidative decarboxylation of benzoylformate. For this purpose the enzyme was obtained in sufficient purity from Pseudomonas putida cells in...
AN EFFICIENT BUTENOLIDE ANNULATION VIA ALPHA'-CHLOROACETOXYLATION OF ENONES USING MANGANESE(III) ACETATE AND CHLOROACETIC ACID DEMIR, AS; AKGUN, H; Tanyeli, Cihangir; SAYRAC, T; WATT, DS (1991-09-01) The alpha'-chloroacetoxylation of alpha,-beta-unsaturated ketones using manganese(III) acetate and chloroacetic acid followed by Arbuzov reaction and intramolecular Horner-Emmons olefination provided a convenient synthesis of annulated 2-buten-4-olides.
Benzaldehyde Lyase-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds Ayhan, Peruze; Demir, Ayhan Sıtkı (Wiley, 2011-03-07) Benzaldehyde lyase from the Pseudomonas fluorescens catalyzes the reaction of aromatic aldehydes with nitroso compounds and furnishes N-arylhydroxamic acids in high yields. Aromatic aldehydes and benzoins are converted into enamine-carbanion-like intermediates prior to their reaction with nitroso compounds. The kinetic resolution of rac-2-hydroxy-1,2-diphenylethanones furnished (S)-benzoins and arylhydroxamic acids with high enantioselectivities and conversions.
Amination/annulation of chlorobutenones with chiral amine compounds: synthesis of 1,2,4-trisubstituted pyrroles Demir, Ayhan Sıtkı; Igdir, AC; Gunay, NB (Elsevier BV, 2005-10-03) A series of 1,2,4-trisubstituted pyrroles have been synthesized in 83-96% yields on treatment of chiral primary amines, amino alcohols and esters of alpha-amino acids with different chlorobutenones in benzene-triethylamine. The conversions proceed without racemization.

Citation Formats

A. S. Demir, N. Camkerten, Z. Gercek, N. Duygu, O. Reis, and E. Arikan, “Butenolide annelation using a manganese(III) oxidation. A synthesis of 4-arylfuran-2(5H)-ones,” TETRAHEDRON, pp. 2441–2448, 1999, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56480.