Enantioselective Synthesis of the C7-C24 Segment of Macrolactin A

A copper-catalyzed annulation reaction to access a variety of isoxazoles from alkenes and oxazete in situ generated from N-alkyl(aryl)-1-(methylthio)-2-nitroethenamine was reported. A plausible mechanism underlying the formation of the product was proposed, which represented a new approach for the construction of isoxazolines. This reaction was capable of tolerating alkenes bearing various substituents, which showed a relatively broad substrate scope with good functional group compatibility.

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From Stereodefined Cyclobutenes to Dienes: Total Syntheses of Ieodomycin D and the Southern Fragment of Macrolactin A

Souris

Misale

Chen

et al. 2015

Org. Lett.

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A copper-promoted flexible synthesis of cyclobutenes carrying simple alkyl chains, enabling even the most hindered nucleophiles to be employed, has been developed. The versatility of this approach was exemplified by a short total synthesis of ieodomycin D and a straightforward preparation of the southeastern fragment of macrolactin A. The latter features a late-stage, double cyclobutene electrocyclic ring opening that directly delivers a bis-diene of defined geometry.

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Enantioselective Synthesis of the C7-C24 Segment of Macrolactin A

Cited by 3 publications

References 11 publications

Crystal and molecular structure of bis(8-phenylmenthyl) 2-(2-methyl-5-oxo-3-cyclohexen-1-yl)propandioate, C42H54O5· CH3CN

Crystal and molecular structure of bis(8-phenylmenthyl) 2-(2-methyl-5-oxo-3-cyclohexen-1-yl)propandioate, C42H54O5· CH3CN

Copper-Catalyzed Annulation Reaction of Alkenes and N-Alkyl(aryl)-1-(methylthio)-2-nitroethenamine: an Approach for the Synthesis of Isoxazole Derivatives

From Stereodefined Cyclobutenes to Dienes: Total Syntheses of Ieodomycin D and the Southern Fragment of Macrolactin A

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