Efficient assembly of 3-substituted oxindole-based isoxazolines leading to the synthesis of (±)-flustraminol-B and related natural product building blocks |
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Authors: | Anand SinghGregory P. Roth |
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Affiliation: | Sanford-Burnham Medical Research Institute at Lake Nona, 6400 Sanger Road, Orlando, FL 32827, USA |
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Abstract: | An efficient synthesis of oxindole-based isoxazolines has been developed and the resulting spirocyclic intermediates have been elaborated to synthetically versatile 3-hydroxy-3-alkyl oxindole building blocks such as the 3-hydroxy-3-methylenecyano-2-oxindoles (6) and γ-amino alcohols (12). Utility of this methodology is demonstrated through the synthesis of pyrrolo[2,3-b]indolines including the marine natural product (±)-flustraminol-B. |
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Keywords: | [3+2] Cycloaddition Isoxazoline 3-Hydroxy oxindole Amino alcohols Pyrrolo[2,3-b]indolines |
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